Mesoionic pesticides

ABSTRACT

Disclosed are compounds of Formula 1, N-oxides, and salts thereof, 
                         
wherein
         X is O or S;   Y is O or S;   A is O, S, NR 3e  or C(R 3c )═C(R 3d );   Z is a direct bond, O, S(O) n , NR 6 , C(R 7 ) 2 O, OC(R 7 ) 2 , C(═X 1 ), C(═X 1 )E, EC(═X 1 ), C(═NOR 8 ) or C(═NN(R 6 ) 2 );   a is 1, 2 or 3;   and R 1 , R 2 , R 3a -R 3e , R 4 , R 5 , R 6 , R 7 , R 8 , X 1  and E are as defined in the disclosure.
 
Also disclosed are compositions containing the compounds of Formula 1 and methods for controlling an invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound or a composition of the invention.

This application is a division of application Ser. No. 13/386,065, filedAug. 3, 2010, which is a national stage entry of PCT/US2010/044274,filed Aug. 3, 2010. PCT/US2010/044274 claims priority benefit fromProvisional Application 61/231,464, filed Aug. 5, 2009.

FIELD OF THE INVENTION

This invention relates to certain pyrimidinium compounds, theirN-oxides, salts and their compositions suitable for agronomic,nonagronomic and animal health uses, methods of their use forcontrolling invertebrate pests such as arthropods in both agronomic andnonagronomic environments, and for treatment of parasite infections inanimals or infestations in the general environment.

BACKGROUND OF THE INVENTION

The control of invertebrate pests is extremely important in achievinghigh crop efficiency. Damage by invertebrate pests to growing and storedagronomic crops can cause significant reduction in productivity andthereby result in increased costs to the consumer. The control ofinvertebrate pests in forestry, greenhouse crops, ornamentals, nurserycrops, stored food and fiber products, livestock, household, turf, woodproducts, and public health is also important. Many products arecommercially available for these purposes, but the need continues fornew compounds that are more effective, less costly, less toxic,environmentally safer or have different sites of action.

The control of animal parasites in animal health is essential,especially in the areas of food production and companion animals.Existing methods of treatment and parasite control are being compromiseddue to growing resistance to many current commercial parasiticides. Thediscovery of more effective ways to control animal parasites istherefore imperative.

U.S. Pat. No. 5,151,427 discloses mesoionic pyrimidinium compounds ofFormula i as anthelmintics

wherein, inter alia, R¹ and R² are independently C₁-C₆ alkyl, R³ is aheteroaromatic 6-membered ring, and R⁴ and R⁵ are independently hydrogenor C₁-C₄ alkyl.

The pyrimidinium compounds of the present invention are not disclosed inthis publication.

SUMMARY OF THE INVENTION

This invention is directed to compounds of Formula 1 (including allstereoisomers), N-oxides, and salts thereof, and compositions containingthem and their use for controlling invertebrate pests:

wherein

-   -   X is O or S;    -   Y is O or S;    -   A is O, S, NR^(3e) or C(R^(3c))═C(R^(3d)), provided that the        C(R^(3c))═C(R^(3d)) moiety is oriented so the carbon atom bonded        to R^(3d) is connected directly to the pyrimidinium ring of        Formula 1;    -   Z is a direct bond, O, S(O)_(n), NR⁶, C(R⁷)₂O, OC(R⁷)₂, C(═X¹),        C(═X¹)E, EC(═X¹), C(═NOR⁸) or C(═NN(R⁶)₂);    -   X¹ is O, S or NR⁹;    -   E is O, S or NR^(9a);    -   R¹ is H, halogen, cyano, CHO, C(═O)OH, C(═O)NH₂ or C(═S)NH₂; or        C₁-C₈ alkyl, C₂-C₈ alkenyl, C₂-C₈ alkynyl, C₃-C₁₀ cycloalkyl,        C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₆-C₁₄        cycloalkylcycloalkyl, C₅-C₁₀ alkylcycloalkylalkyl or C₃-C₆        cycloalkenyl, each unsubstituted or substituted with at least        one substituent independently selected from the group consisting        of halogen, cyano, nitro, CHO, C(═O)OH, C(═O)NH₂, C(═O)R¹⁰,        C(═O)OR¹¹, C(═O)NR¹²R¹³, C(═O)NR²¹NR²²R²³, OR¹¹, S(O)_(n)R¹⁰,        SO₂NR¹²R¹³, S(═O)(═NR²¹)R²², Si(R¹⁰)₃ and Z¹Q^(t); or a 3- to        10-membered ring or a 7- to 11-membered ring system, each ring        or ring system containing ring members selected from carbon        atoms and up to 4 heteroatoms independently selected from up to        2 O, up to 2 S, and up to 4 N, wherein up to 3 carbon atom ring        members are independently selected from C(═O) and C(═S) and the        sulfur atom ring members are independently selected from        S(═O)_(u)(═NR²⁴)_(z), each ring or ring system optionally        substituted with up to 5 substituents independently selected        from R¹⁴; provided that when R¹ is halogen, then Z is a direct        bond, S(═O), S(═O)₂, OC(R⁷)₂, C(═X¹), EC(═X¹), C(═NOR⁸) or        C(═NN(R⁶)₂);    -   R² is H, halogen, cyano, hydroxy, amino, nitro, OCN, SCN, CHO,        C(═O)OH, C(═O)NH₂, C(═S)NH₂, SO₂NH₂, C(═O)R¹⁸, C(═O)OR¹⁸, NHR¹⁸,        NR¹⁸R¹⁹, C(═O)NR²¹R¹⁹, C(═S)NR²¹R¹⁹, SO₂NR²¹R¹⁹, OC(═O)R²¹,        OC(═O)OR¹⁸, OC(═O)NR²¹R¹⁹, N(R²¹)C(═O)R²¹, N(R²¹)C(═O)OR¹⁹,        N(R²¹)C(═O)NR²¹R²², OSO₂R¹⁸, OSO₂NR²¹R²², NR²¹SO₂R¹⁸,        NR²¹SO₂NR²¹R²² or Si(R¹⁸R¹⁹R²⁰); or C₁-C₈ alkyl, C₂-C₈ alkenyl,        C₂-C₈ alkynyl, C₃-C₁₀ cycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀        cycloalkylalkyl, C₆-C₁₄ cycloalkylcycloalkyl, C₅-C₁₀        alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl, C₁-C₈ alkoxy, C₃-C₈        cycloalkoxy, C₄-C₁₀ cycloalkylalkoxy, C₂-C₈ alkenyloxy, C₂-C₈        alkynyloxy, C₁-C₈ alkylthio, C₁-C₈ alkylsulfinyl, C₁-C₈        alkylsulfonyl, C₃-C₈ cycloalkylthio, C₃-C₈ cycloalkylsulfinyl,        C₃-C₈ cycloalkylsulfonyl, C₄-C₁₀ cycloalkylalkylthio, C₄-C₁₀        cycloalkylalkylsulfinyl, C₄-C₁₀ cycloalkylalkylsulfonyl, C₂-C₈        alkenylthio, C₂-C₈ alkenylsulfinyl, C₂-C₈ alkenylsulfonyl, C₂-C₈        alkynylthio, C₂-C₈ alkynylsulfinyl or C₂-C₈ alkynylsulfonyl,        each unsubstituted or substituted with at least one substituent        independently selected from the group consisting of halogen,        cyano, nitro, CHO, C(═O)OH, C(═O)NH₂, C(═O)R¹⁰, C(═O)OR¹¹,        C(═O)NR¹²R¹³, OR¹¹, S(O)_(n)R¹⁰, SO₂NR¹²R¹³ and Si(R¹⁰)₃; or a        3- to 10-membered ring or a 7- to 11-membered ring system, each        ring or ring system containing ring members selected from carbon        atoms and up to 4 heteroatoms independently selected from up to        2 O, up to 2 S, and up to 4 N, wherein up to 3 carbon atom ring        members are independently selected from C(═O) and C(═S) and the        sulfur atom ring members are independently selected from        S(═O)_(u)(═NR²⁴)_(z), each ring or ring system optionally        substituted with up to 5 substituents independently selected        from R¹⁵;    -   R^(3a), R^(3b), R^(3c) and R^(3d) are independently H, halogen,        cyano, hydroxy, amino, nitro, SF₅, OCN, SCN, CHO, C(═O)OH,        C(═O)NH₂, C(═S)NH₂, SO₂NH₂, C(═O)R¹⁸, C(═O)OR¹⁸, NHR¹⁸, NR¹⁸R¹⁹,        C(═O)NR²¹R¹⁹, C(═S)NR²¹R¹⁹, SO₂NR²¹R¹⁹, OC(═O)R²¹, OC(═O)OR¹⁸,        OC(═O)NR²¹R¹⁹, N(R²¹)C(═O)R²¹, N(R²¹)C(═O)OR¹⁹,        N(R²¹)C(═O)NR²¹R²², OSO₂R¹⁸, OSO₂NR²¹R²², NR²¹SO₂R¹⁸,        NR²¹SO₂NR²¹R²², Si(R¹⁸R¹⁹R²⁰) or Z¹Q^(t); or C₁-C₈ alkyl, C₂-C₈        alkenyl, C₂-C₈ alkynyl, C₃-C₁₀ cycloalkyl, C₄-C₁₀        alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₆-C₁₄        cycloalkylcycloalkyl, C₅-C₁₀ alkylcycloalkylalkyl, C₃-C₈        cycloalkenyl, C₁-C₈ alkoxy, C₃-C₈ cycloalkoxy, C₄-C₁₀        cycloalkylalkoxy, C₂-C₈ alkenyloxy, C₂-C₈ alkynyloxy, C₁-C₈        alkylthio, C₁-C₈ alkylsulfinyl, C₁-C₈ alkylsulfonyl, C₃-C₈        cycloalkylthio, C₃-C₈ cycloalkylsulfinyl, C₃-C₈        cycloalkylsulfonyl, C₄-C₁₀ cycloalkylalkylthio, C₄-C₁₀        cycloalkylalkylsulfinyl, C₄-C₁₀ cycloalkylalkylsulfonyl, C₂-C₈        alkenylthio, C₂-C₈ alkenylsulfinyl, C₂-C₈ alkenylsulfonyl, C₂-C₈        alkynylthio, C₂-C₈ alkynylsulfinyl or C₂-C₈ alkynylsulfonyl,        each unsubstituted or substituted with at least one substituent        independently selected from R¹⁷; or R^(3a) and R^(3b), or R^(3b)        and R^(3c), or R^(3c) and R^(3d) are taken together with the        adjacent carbon atoms to which they are attached to form a 5- to        7-membered carbocyclic or heterocyclic ring, each ring        containing ring members selected from carbon atoms and up to 3        heteroatoms independently selected from up to 2 O, up to 2 S,        and up to 3 N, wherein up to 2 carbon atom ring members are        independently selected from C(═O) and C(═S) and the sulfur atom        ring members are independently selected from S(═O)_(n), each        ring optionally substituted with up to 3 substituents        independently selected from the group consisting of halogen,        cyano, hydroxy, amino, nitro, C(═O)OH, C(═O)NH₂, SO₂NH₂, C₁-C₄        alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄        alkynyl, C₂-C₄ haloalkynyl, C₃-C₇ cycloalkyl, C₃-C₇        halocycloalkyl, C₄-C₈ alkylcycloalkyl, C₄-C₈        haloalkylcycloalkyl, C₄-C₈ cycloalkylalkyl, C₄-C₈        halocycloalkylalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₂-C₆        alkoxycarbonyl, C₂-C₆ haloalkoxycarbonyl, C₂-C₆ alkylcarbonyl        and C₂-C₆ haloalkylcarbonyl;    -   R^(3e) is H, hydroxy, amino, CHO, C(═O)NH₂, C(═S)NH₂, SO₂NH₂,        C(═O)R¹⁸, C(═O)OR¹⁸, NHR¹⁸, NR¹⁸R¹⁹, C(═O)NR²¹R¹⁹, C(═S)NR²¹R¹⁹,        SO₂NR²¹R¹⁹, OC(═O)R²¹, OC(═O)OR¹⁸, OC(═O)NR²¹R¹⁹,        N(R²¹)C(═O)R²¹, N(R²¹)C(═O)OR¹⁹, N(R²¹)C(═O)NR²¹R²², OSO₂R¹⁸,        OSO₂NR²¹R²², NR²¹SO₂R¹⁸, NR²¹SO₂NR²¹R²², Si(R¹⁸R¹⁹R²⁰) or        Z¹Q^(t); or C₁-C₈ alkyl, C₂-C₈ alkenyl, C₂-C₈ alkynyl, C₃-C₁₀        cycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl,        C₆-C₁₄ cycloalkylcycloalkyl, C₅-C₁₀ alkylcycloalkylalkyl, C₃-C₈        cycloalkenyl, C₁-C₈ alkoxy, C₃-C₈ cycloalkoxy, C₄-C₁₀        cycloalkylalkoxy, C₂-C₈ alkenyloxy, C₂-C₈ alkynyloxy, C₁-C₈        alkylsulfinyl, C₁-C₈ alkylsulfonyl, C₃-C₈ cycloalkylsulfinyl,        C₃-C₈ cycloalkylsulfonyl, C₄-C₁₀ cycloalkylalkylsulfinyl, C₄-C₁₀        cycloalkylalkylsulfonyl, C₂-C₈ alkenylsulfinyl, C₂-C₈        alkenylsulfonyl, C₂-C₈ alkynylsulfinyl or C₂-C₈ alkynylsulfonyl,        each unsubstituted or substituted with at least one substituent        independently selected from R¹⁷; or R^(3e) and R^(3b) are taken        together with the adjacent carbon atoms to which they are        attached to form a 5- to 7-membered carbocyclic or heterocyclic        ring, each ring containing ring members selected from carbon        atoms and up to 3 heteroatoms independently selected from up to        2 O, up to 2 S, and up to 3 N, wherein up to 2 carbon atom ring        members are independently selected from C(═O) and C(═S) and the        sulfur atom ring members are independently selected from        S(═O)_(n), each ring optionally substituted with up to 3        substituents independently selected from the group consisting of        halogen, cyano, hydroxy, amino, nitro, C(═O)OH, C(═O)NH₂,        SO₂NH₂, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄        haloalkenyl, C₂-C₄ alkynyl, C₂-C₄ haloalkynyl, C₃-C₇ cycloalkyl,        C₃-C₇ halocycloalkyl, C₄-C₈ alkylcycloalkyl, C₄-C₈        haloalkylcycloalkyl, C₄-C₈ cycloalkylalkyl, C₄-C₈        halocycloalkylalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₂-C₆        alkoxycarbonyl, C₂-C₆ haloalkoxycarbonyl, C₂-C₆ alkylcarbonyl        and C₂-C₆ haloalkylcarbonyl;    -   each R⁴ and R⁵ is independently H, halogen, cyano, hydroxy,        amino, nitro, OCN, SCN, CHO, C(═O)OH, C(═O)NH₂, C(═S)NH₂ or        SO₂NH₂; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₈        cycloalkyl, C₄-C₈ alkylcycloalkyl, C₄-C₈ cycloalkylalkyl, C₆-C₁₂        cycloalkylcycloalkyl, C₅-C₈ alkylcycloalkylalkyl, C₃-C₆        cycloalkenyl, C₁-C₆ alkoxy, C₃-C₆ cycloalkoxy, C₄-C₈        cycloalkylalkoxy, C₂-C₆ alkenyloxy or C₂-C₆ alkynyloxy, each        unsubstituted or substituted with at least one substituent        independently selected from the group consisting of halogen,        cyano, nitro, CHO, C(═O)OH, C(═O)NH₂, C(═O)R¹⁰, C(═O)OR¹¹,        C(═O)NR¹²R¹³, OR¹¹, S(O)_(n)R¹⁰, SO₂NR¹²R¹³ and Si(R¹⁰)₃; or    -   R⁴ and R⁵ are taken together with the carbon atom to which they        are attached to form a 3- to 7-membered ring containing ring        members selected from carbon atoms and up to 2 heteroatoms        independently selected from one O, one S, and up to 2 N, wherein        up to 2 carbon atom ring members are independently selected from        C(═O) and C(═S) and the sulfur atom ring member is selected from        S, S(O) or S(O)₂, said ring optionally substituted with up to 4        substituents independently selected from the group consisting of        halogen, cyano and C₁-C₄ alkyl;    -   each R⁶ is independently H; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆        alkynyl, C₃-C₈ cycloalkyl, C₄-C₈ alkylcycloalkyl, C₄-C₈        cycloalkylalkyl, C₆-C₁₀ cycloalkylcycloalkyl, C₅-C₁₀        alkylcycloalkylalkyl, C₃-C₆ cycloalkenyl, C₂-C₆ alkylcarbonyl or        C₂-C₆ alkoxycarbonyl, each unsubstituted or substituted with at        least one substituent independently selected from the group        consisting of halogen, cyano, nitro, CHO, C(═O)OH, C(═O)NH₂,        C(═O)R¹⁰, C(═O)OR¹¹, C(═O)NR¹²R¹³, OR¹¹, S(O)_(n)R¹⁰, SO₂NR¹²R¹³        and Si(R¹⁰)₃; or    -   two R⁶ substituents are taken together with the nitrogen atom to        which they are attached to form a 3- to 7-membered ring        containing ring members selected from carbon atoms and up to 2        heteroatoms independently selected from one O, one S, and up to        2 N, wherein up to 2 carbon atom ring members are independently        selected from C(═O) and C(═S) and the sulfur atom ring member is        selected from S, S(O) or S(O)₂, said ring optionally substituted        with up to 4 substituents independently selected from the group        consisting of halogen, cyano and C₁-C₄ alkyl;    -   each R⁷ and R⁸ is independently H; or C₁-C₆ alkyl, C₂-C₆        alkenyl, C₂-C₆ alkynyl, C₃-C₈ cycloalkyl, C₄-C₈ alkylcycloalkyl,        C₄-C₈ cycloalkylalkyl, C₆-C₁₀ cycloalkylcycloalkyl, C₅-C₁₀        alkylcycloalkylalkyl, C₃-C₆ cycloalkenyl, C₂-C₆ alkylcarbonyl or        C₂-C₆ alkoxycarbonyl, each unsubstituted or substituted with at        least one substituent independently selected from the group        consisting of halogen, cyano, nitro, CHO, C(═O)OH, C(═O)NH₂,        C(═O)R¹⁰, C(═O)OR¹¹, C(═O)NR¹²R¹³, OR¹¹, S(O)_(n)R¹⁰, SO₂NR¹²R¹³        and Si(R¹⁰)₃;    -   each R⁹ is independently C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆        alkynyl, C₃-C₈ cycloalkyl, C₄-C₈ alkylcycloalkyl, C₄-C₈        cycloalkylalkyl, C₆-C₁₀ cycloalkylcycloalkyl, C₅-C₁₀        alkylcycloalkylalkyl, C₃-C₆ cycloalkenyl, C₂-C₆ alkylcarbonyl or        C₂-C₆ alkoxycarbonyl, each unsubstituted or substituted with at        least one substituent independently selected from the group        consisting of halogen, cyano, nitro, CHO, C(═O)OH, C(═O)NH₂,        C(═O)R¹⁰, C(═O)OR¹¹, C(═O)NR¹²R¹³, OR¹¹, S(O)_(n)R¹⁰, SO₂NR¹²R¹³        and Si(R¹⁰)₃;    -   each R^(9a) is independently H; or C₁-C₆ alkyl, C₂-C₆ alkenyl,        C₂-C₆ alkynyl, C₃-C₈ cycloalkyl, C₄-C₈ alkylcycloalkyl, C₄-C₈        cycloalkylalkyl, C₆-C₁₀ cycloalkylcycloalkyl, C₅-C₁₀        alkylcycloalkylalkyl, C₃-C₆ cycloalkenyl, C₂-C₆ alkylcarbonyl or        C₂-C₆ alkoxycarbonyl, each unsubstituted or substituted with at        least one substituent independently selected from the group        consisting of halogen, cyano, nitro, CHO, C(═O)OH, C(═O)NH₂,        C(═O)R¹⁰, C(═O)OR¹¹, C(═O)NR¹²R¹³, OR¹¹, S(O)_(n)R¹⁰, SO₂NR¹²R¹³        and Si(R¹⁰)₃;    -   each R¹⁰ and R¹¹ is independently C₁-C₆ alkyl, C₂-C₆ alkenyl,        C₂-C₆ alkynyl, C₃-C₈ cycloalkyl, C₄-C₈ alkylcycloalkyl, C₄-C₈        cycloalkylalkyl, C₆-C₁₀ cycloalkylcycloalkyl, C₅-C₁₀        alkylcycloalkylalkyl or C₃-C₆ cycloalkenyl, each unsubstituted        or substituted with at least one substituent independently        selected from the group consisting of halogen, cyano, nitro,        CHO, C(═O)OH, C(═O)NH₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄        alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄        haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl,        C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino,        C₂-C₄ alkoxyalkyl, C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl,        C₂-C₆ alkylcarbonyloxy, C₂-C₆ alkylcarbonylthio, C₂-C₆        alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl and C₃-C₆        trialkylsilyl; or phenyl or a 5- or 6-membered heteroaromatic        ring, each unsubstituted or substituted with at least one        substituent independently selected from the group consisting of        C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl,        C₃-C₈ cycloalkyl, C₄-C₈ alkylcycloalkyl, C₄-C₈ cycloalkylalkyl,        C₆-C₁₀ cycloalkylcycloalkyl, C₅-C₁₀ alkylcycloalkylalkyl, C₃-C₆        cycloalkenyl, halogen, cyano, nitro, CHO, C(═O)OH, C(═O)NH₂,        C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄        alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄        haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl, C₁-C₄ alkylamino,        C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₂-C₄ alkoxyalkyl,        C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆        alkylcarbonyloxy, C₂-C₆ alkylcarbonylthio, C₂-C₆        alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl and C₃-C₆        trialkylsilyl;    -   each R¹² and R¹³ is independently C₁-C₆ alkyl, C₂-C₆ alkenyl,        C₂-C₆ alkynyl, C₃-C₈ cycloalkyl, C₄-C₈ alkylcycloalkyl, C₄-C₈        cycloalkylalkyl, C₆-C₁₀ cycloalkylcycloalkyl, C₅-C₁₀        alkylcycloalkylalkyl or C₃-C₆ cycloalkenyl, each unsubstituted        or substituted with at least one substituent independently        selected from the group consisting of halogen, cyano, nitro,        CHO, C(═O)OH, C(═O)NH₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄        alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄        haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl,        C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino,        C₂-C₄ alkoxyalkyl, C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl,        C₂-C₆ alkylcarbonyloxy, C₂-C₆ alkylcarbonylthio, C₂-C₆        alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl and C₃-C₆        trialkylsilyl; or phenyl or a 5- or 6-membered heteroaromatic        ring, each unsubstituted or substituted with at least one        substituent independently selected from the group consisting of        C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl,        C₃-C₈ cycloalkyl, C₄-C₈ alkylcycloalkyl, C₄-C₈ cycloalkylalkyl,        C₆-C₁₀ cycloalkylcycloalkyl, C₅-C₁₀ alkylcycloalkylalkyl, C₃-C₆        cycloalkenyl, halogen, cyano, nitro, CHO, C(═O)OH, C(═O)NH₂,        C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄        alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄        haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl, C₁-C₄ alkylamino,        C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₂-C₄ alkoxyalkyl,        C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆        alkylcarbonyloxy, C₂-C₆ alkylcarbonylthio, C₂-C₆        alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl and C₃-C₆        trialkylsilyl; or    -   R¹² and R¹³ are taken together with the nitrogen atom to which        they are attached to form a 3- to 7-membered ring containing        ring members selected from carbon atoms and up to 2 heteroatoms        independently selected from one O, one S, and up to 2 N, wherein        up to 2 carbon atom ring members are independently selected from        C(═O) and C(═S) and the sulfur atom ring member is selected from        S, S(O) or S(O)₂, said ring optionally substituted with up to 4        substituents independently selected from the group consisting of        halogen, cyano and C₁-C₄ alkyl;    -   each R¹⁴ is independently halogen, cyano, hydroxy, amino, nitro,        SF₅, OCN, SCN, CHO, C(═O)OH, C(═O)NH₂, C(═S)NH₂, SO₂NH₂,        C(═O)R¹⁸, C(═O)OR¹⁸, NHR¹⁸, NR¹⁸R¹⁹, C(═O)NR²¹R¹⁹,        C(═O)NR²¹NR²²R²³, C(═S)NR²¹R¹⁹, SO₂NR²¹R¹⁹, OC(═O)R²¹,        OC(═O)OR¹⁸, OC(═O)NR²¹R¹⁹, N(R²¹)C(═O)R²¹, N(R²¹)C(═O)OR¹⁹,        N(R²¹)C(═O)NR²¹R²², OSO₂R¹⁸, OSO₂NR²¹R²², NR²¹SO₂R¹⁸,        NR²¹SO₂NR²¹R²², Si(R¹⁸R¹⁹R²⁰), C(═NR²¹)R²², C(═NOR²¹)R²²,        C(═NNR²¹R²²)R²³, C(═NN(C(═O)R¹⁹)R²¹)R²²,        C(═NN(C(═O)OR¹⁹)R²¹)R²², ON═CR²¹R²², ONR²¹R²², S(═O)(═NR²¹)R²²,        SO₂NR²¹C(═O)NR²²R²³, P(═X²)R¹⁸R¹⁹, OP(═X²)R¹⁸R¹⁹,        OP(═X²)(OR¹⁸)R¹⁹, OP(═X²)(OR¹⁸)OR¹⁹, N═CR²¹R²², NR²¹N═CR²²R²³,        NR²¹NR²²R²³, NR²¹C(═X²)NR²²R²³, NR²¹C(═NR²¹)NR²²R²³,        NR²¹NR²¹C(═X²)NR²²R²³, NR²¹NR²¹SO₂NR²²R²³, Z¹Q^(t) or        Z¹Q^(i)Z¹Q^(t); or C₁-C₈ alkyl, C₂-C₈ alkenyl, C₂-C₈ alkynyl,        C₃-C₁₀ cycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀        cycloalkylalkyl, C₆-C₁₄ cycloalkylcycloalkyl, C₅-C₁₀        alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl, C₁-C₈ alkoxy, C₃-C₈        cycloalkoxy, C₄-C₁₀ cycloalkylalkoxy, C₂-C₈ alkenyloxy, C₂-C₈        alkynyloxy, C₁-C₈ alkylthio, C₁-C₈ alkylsulfinyl, C₁-C₈        alkylsulfonyl, C₃-C₈ cycloalkylthio, C₃-C₈ cycloalkylsulfinyl,        C₃-C₈ cycloalkylsulfonyl, C₄-C₁₀ cycloalkylalkylthio, C₄-C₁₀        cycloalkylalkylsulfinyl, C₄-C₁₀ cycloalkylalkylsulfonyl, C₂-C₈        alkenylthio, C₂-C₈ alkenylsulfinyl, C₂-C₈ alkenylsulfonyl, C₂-C₈        alkynylthio, C₂-C₈ alkynylsulfinyl or C₂-C₈ alkynylsulfonyl,        each unsubstituted or substituted with at least one substituent        independently selected from R¹⁷; or    -   two R¹⁴ substituents on adjacent ring atoms are taken together        with the adjacent ring atoms to form a 5- to 7-membered        carbocyclic or heterocyclic ring, each ring containing ring        members selected from carbon atoms and up to 3 heteroatoms        independently selected from up to 2 O, up to 2 S, and up to 3 N,        wherein up to 2 carbon atom ring members are independently        selected from C(═O) and C(═S) and the sulfur atom ring members        are independently selected from S(═O)_(n), each ring optionally        substituted with up to 3 substituents independently selected        from the group consisting of halogen, cyano, hydroxy, amino,        nitro, C(═O)OH, C(═O)NH₂, SO₂NH₂, C₁-C₄ alkyl, C₁-C₄ haloalkyl,        C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₂-C₄        haloalkynyl, C₃-C₇ cycloalkyl, C₃-C₇ halocycloalkyl, C₄-C₈        alkylcycloalkyl, C₄-C₈ haloalkylcycloalkyl, C₄-C₈        cycloalkylalkyl, C₄-C₈ halocycloalkylalkyl, C₁-C₆ alkoxy, C₁-C₆        haloalkoxy, C₂-C₆ alkoxycarbonyl, C₂-C₆ haloalkoxycarbonyl,        C₂-C₆ alkylcarbonyl and C₂-C₆ haloalkylcarbonyl;    -   each X² is independently O or S;    -   each Z¹ is independently a direct bond, O, S(O)_(n), NR⁶,        C(R⁷)₂, C(R⁷)═C(R⁷), C≡C, C(R⁷)₂O, OC(R⁷)₂, C(═X¹), C(═X¹)E,        EC(═X¹), C(═NOR⁸) or C(═NN(R⁶)₂);    -   each Q^(i) is independently a 3- to 10-membered ring or a 7- to        11-membered ring system, each ring or ring system containing        ring members selected from carbon atoms and up to 4 heteroatoms        independently selected from up to 2 O, up to 2 S, and up to 4 N,        wherein up to 3 carbon atom ring members are independently        selected from C(═O) and C(═S) and the sulfur atom ring members        are independently selected from S(═O)_(u)(═NR²⁴)_(z), each ring        or ring system optionally substituted with up to 4 substituents        independently selected from the group consisting of halogen,        cyano, nitro, CHO, C(═O)OH, C(═O)NH₂, C(═O)R¹⁰, C(═O)OR¹¹,        C(═O)NR¹²R¹³, OR¹¹, S(O)_(n)R¹⁰, SO₂NR¹²R¹³, Si(R¹⁰)₃ and R¹⁶;    -   each Q^(t) is independently a 3- to 10-membered ring or a 7- to        11-membered ring system, each ring or ring system containing        ring members selected from carbon atoms and up to 4 heteroatoms        independently selected from up to 2 O, up to 2 S, and up to 4 N,        wherein up to 3 carbon atom ring members are independently        selected from C(═O) and C(═S) and the sulfur atom ring members        are independently selected from S(═O)_(u)(═NR²⁴)_(z), each ring        or ring system optionally substituted with up to 5 substituents        independently selected from the group consisting of halogen,        cyano, nitro, CHO, C(═O)OH, C(═O)NH₂, C(═O)R¹⁰, C(═O)OR¹¹,        C(═O)NR¹²R¹³, C(═O)NR²¹NR²²R²³, OR¹¹, S(O)_(n)R¹⁰, SO₂NR¹²R¹³,        S(═O)(═NR²¹)R²², Si(R¹⁰)₃ and R¹⁶;    -   each R¹⁵ is independently halogen, cyano, hydroxy, amino, nitro,        SF₅, OCN, SCN, CHO, C(═O)OH, C(═O)NH₂, C(═S)NH₂, SO₂NH₂,        C(═O)R¹⁸, C(═O)OR¹⁸, NHR¹⁸, NR¹⁸R¹⁹, C(═O)NR²¹R¹⁹,        C(═O)NR²¹NR²²R²³, C(═S)NR²¹R¹⁹, SO₂NR²¹R¹⁹, S(═O)(═NR²¹)R²²,        OC(═O)R²¹, OC(═O)OR¹⁸, OC(═O)NR²¹R¹⁹, N(R²¹)C(═O)R²¹,        N(R²¹)C(═O)OR¹⁹, N(R²¹)C(═O)NR²¹R²², OSO₂R¹⁸, OSO₂NR²¹R²²,        NR²¹SO₂R¹⁸, NR²¹SO₂NR²¹R²², Si(R¹⁸R¹⁹R²⁰) or Z¹Q^(t); or C₁-C₈        alkyl, C₂-C₈ alkenyl, C₂-C₈ alkynyl, C₃-C₁₀ cycloalkyl, C₄-C₁₀        alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₆-C₁₄        cycloalkylcycloalkyl, C₅-C₁₀ alkylcycloalkylalkyl, C₃-C₈        cycloalkenyl, C₁-C₈ alkoxy, C₃-C₈ cycloalkoxy, C₄-C₁₀        cycloalkylalkoxy, C₂-C₈ alkenyloxy, C₂-C₈ alkynyloxy, C₁-C₈        alkylthio, C₁-C₈ alkylsulfinyl, C₁-C₈ alkylsulfonyl, C₃-C₈        cycloalkylthio, C₃-C₈ cycloalkylsulfinyl, C₃-C₈        cycloalkylsulfonyl, C₄-C₁₀ cycloalkylalkylthio, C₄-C₁₀        cycloalkylalkylsulfinyl, C₄-C₁₀ cycloalkylalkylsulfonyl, C₂-C₈        alkenylthio, C₂-C₈ alkenylsulfinyl, C₂-C₈ alkenylsulfonyl, C₂-C₈        alkynylthio, C₂-C₈ alkynylsulfinyl or C₂-C₈ alkynylsulfonyl,        each unsubstituted or substituted with at least one substituent        independently selected from R¹⁷; or    -   two R¹⁵ substituents on adjacent ring atoms are taken together        with the adjacent ring atoms to form a 5- to 7-membered        carbocyclic or heterocyclic ring, each ring containing ring        members selected from carbon atoms and up to 3 heteroatoms        independently selected from up to 2 O, up to 2 S, and up to 3 N,        wherein up to 2 carbon atom ring members are independently        selected from C(═O) and C(═S) and the sulfur atom ring members        are independently selected from S(═O)_(n), each ring optionally        substituted with up to 3 substituents independently selected        from the group consisting of halogen, cyano, hydroxy, amino,        nitro, C(═O)OH, C(═O)NH₂, SO₂NH₂, C₁-C₄ alkyl, C₁-C₄ haloalkyl,        C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₂-C₄        haloalkynyl, C₃-C₇ cycloalkyl, C₃-C₇ halocycloalkyl, C₄-C₈        alkylcycloalkyl, C₄-C₈ haloalkylcycloalkyl, C₄-C₈        cycloalkylalkyl, C₄-C₈ halocycloalkylalkyl, C₁-C₆ alkoxy, C₁-C₆        haloalkoxy, C₂-C₆ alkoxycarbonyl, C₂-C₆ haloalkoxycarbonyl,        C₂-C₆ alkylcarbonyl and C₂-C₆ haloalkylcarbonyl;    -   each R¹⁶ is independently C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆        alkynyl, C₃-C₈ cycloalkyl, C₄-C₈ alkylcycloalkyl, C₄-C₈        cycloalkylalkyl, C₆-C₁₀ cycloalkylcycloalkyl, C₅-C₁₀        alkylcycloalkylalkyl or C₃-C₆ cycloalkenyl, each unsubstituted        or substituted with at least one substituent independently        selected from the group consisting of halogen, cyano, nitro,        CHO, C(═O)OH, C(═O)NH₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄        alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄        haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl,        C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino,        C₂-C₄ alkoxyalkyl, C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl,        C₂-C₆ alkylcarbonyloxy, C₂-C₆ alkylcarbonylthio, C₂-C₆        alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl and C₃-C₆        trialkylsilyl; or phenyl or a 5- or 6-membered heteroaromatic        ring, each unsubstituted or substituted with at least one        substituent independently selected from the group consisting of        C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₈ cycloalkyl,        C₄-C₈ alkylcycloalkyl, C₄-C₈ cycloalkylalkyl, C₆-C₁₀        cycloalkylcycloalkyl, C₅-C₁₀ alkylcycloalkylalkyl, C₃-C₆        cycloalkenyl, halogen, cyano, nitro, CHO, C(═O)OH, C(═O)NH₂,        C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄        alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄        haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl, C₁-C₄ alkylamino,        C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₂-C₄ alkoxyalkyl,        C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆        alkylcarbonyloxy, C₂-C₆ alkylcarbonylthio, C₂-C₆        alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl and C₃-C₆        trialkylsilyl;    -   each R¹⁷ is independently halogen, cyano, nitro, OH, CHO,        C(═O)OH, C(═O)NH₂, C(═O)R¹⁰, C(═O)OR¹¹, C(═O)NR¹²R¹³, OR¹¹,        S(O)_(n)R¹⁰, SO₂NR¹²R¹³, Si(R¹⁰)₃ or Z¹Q^(t);    -   each R¹⁸, R¹⁹ and R²⁰ is independently Q^(t); or C₁-C₆ alkyl,        C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₈ cycloalkyl, C₄-C₈        alkylcycloalkyl, C₄-C₈ cycloalkylalkyl, C₆-C₁₀        cycloalkylcycloalkyl, C₅-C₁₀ alkylcycloalkylalkyl or C₃-C₆        cycloalkenyl, each unsubstituted or substituted with at least        one substituent independently selected from R¹⁷;    -   each R²¹ is independently Q^(t) or H; or C₁-C₆ alkyl, C₂-C₆        alkenyl, C₂-C₆ alkynyl, C₃-C₈ cycloalkyl, C₄-C₈ alkylcycloalkyl,        C₄-C₈ cycloalkylalkyl, C₆-C₁₀ cycloalkylcycloalkyl, C₅-C₁₀        alkylcycloalkylalkyl or C₃-C₆ cycloalkenyl, each unsubstituted        or substituted with at least one substituent independently        selected from R¹⁷;    -   each R²² and R²³ is independently Q^(t) or H; or C₁-C₆ alkyl,        C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₈ cycloalkyl, C₄-C₈        alkylcycloalkyl, C₄-C₈ cycloalkylalkyl, C₆-C₁₀        cycloalkylcycloalkyl, C₅-C₁₀ alkylcycloalkylalkyl or C₃-C₆        cycloalkenyl, each unsubstituted or substituted with at least        one substituent independently selected from R¹⁷; or    -   R²² and R²³ are taken together with the nitrogen atom to which        they are attached to form a 3- to 7-membered ring containing        ring members selected from carbon atoms and up to 2 heteroatoms        independently selected from one O, one S, and up to 2 N, wherein        up to 2 carbon atom ring members are independently selected from        C(═O) and C(═S) and the sulfur atom ring member is selected from        S, S(O) or S(O)₂, said ring optionally substituted with up to 4        substituents independently selected from the group consisting of        halogen, cyano and C₁-C₄ alkyl;    -   each R²⁴ is independently H, cyano, OCN, SCN, CHO, C(═O)OH,        C(═O)NH₂, C(═S)NH₂, SO₂NH₂, C(═O)R¹⁸, C(═O)OR¹⁸, NHR¹⁸, NR¹⁸R¹⁹,        C(═O)NR²¹R¹⁹, C(═S)NR²¹R¹⁹, SO₂NR²¹R¹⁹, OC(═O)R²¹, OC(═O)OR¹⁸,        OC(═O)NR²¹R¹⁹, N(R²¹)C(═O)R²¹, N(R²¹)C(═O)OR¹⁹,        N(R²¹)C(═O)NR²¹R²², OSO₂R¹⁸, OSO₂NR²¹R²², NR²¹SO₂R¹⁸,        NR²¹SO₂NR²¹R²², Si(R¹⁸R¹⁹R²⁰) or Z¹Q^(t); or C₁-C₈ alkyl, C₂-C₈        alkenyl, C₂-C₈ alkynyl, C₃-C₁₀ cycloalkyl, C₄-C₁₀        alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₆-C₁₄        cycloalkylcycloalkyl, C₅-C₁₀ alkylcycloalkylalkyl, C₃-C₈        cycloalkenyl, C₁-C₈ alkoxy, C₃-C₈ cycloalkoxy, C₄-C₁₀        cycloalkylalkoxy, C₂-C₈ alkenyloxy, C₂-C₈ alkynyloxy, C₁-C₈        alkylthio, C₁-C₈ alkylsulfinyl, C₁-C₈ alkylsulfonyl, C₃-C₈        cycloalkylthio, C₃-C₈ cycloalkylsulfinyl, C₃-C₈        cycloalkylsulfonyl, C₄-C₁₀ cycloalkylalkylthio, C₄-C₁₀        cycloalkylalkylsulfinyl, C₄-C₁₀ cycloalkylalkylsulfonyl, C₂-C₈        alkenylthio, C₂-C₈ alkenylsulfinyl, C₂-C₈ alkenylsulfonyl, C₂-C₈        alkynylthio, C₂-C₈ alkynylsulfinyl or C₂-C₈ alkynylsulfonyl,        each unsubstituted or substituted with at least one substituent        independently selected from R¹⁷;    -   a is 1, 2 or 3;    -   each n is independently 0, 1 or 2; and    -   u and z in each instance of S(═O)_(u)(═NR²⁴)_(z) are        independently 0, 1 or 2, provided that the sum of u and z in        each instance of S(═O)_(u)(═NR²⁴)_(z) is 0, 1 or 2.

This invention is also directed to such compounds of Formula 1(including all stereoisomers), N-oxides, and salts thereof, andcompositions containing them and their use for controlling invertebratepests as described above, and further herein, provided that when A is O,S, NCH₃ or C(R^(3c))═C(R^(3d)), R^(3c) is H or F, and R^(3d) is H, F,CF₂H or CF₃, then at least one of R^(3a) or R^(3b) is other than H.

This invention also provides a composition comprising a compound ofFormula 1, an N-oxide, or a salt thereof, and at least one additionalcomponent selected from the group consisting of surfactants, soliddiluents and liquid diluents. In one embodiment, this invention alsoprovides a composition for controlling an invertebrate pest comprising acompound of Formula 1, an N-oxide, or a salt thereof, and at least oneadditional component selected from the group consisting of surfactants,solid diluents and liquid diluents, said composition further comprisingat least one additional biologically active compound or agent.

This invention provides a method for controlling an invertebrate pestcomprising contacting the invertebrate pest or its environment with abiologically effective amount of a compound of Formula 1, an N-oxide, ora salt thereof (e.g., as a composition described herein). This inventionalso relates to such method wherein the invertebrate pest or itsenvironment is contacted with a composition comprising a biologicallyeffective amount of a compound of Formula 1, an N-oxide, or a saltthereof, and at least one additional component selected from the groupconsisting of surfactants, solid diluents and liquid diluents, saidcomposition optionally further comprising a biologically effectiveamount of at least one additional biologically active compound or agent.

This invention also provides a method for controlling an invertebratepest comprising contacting the invertebrate pest or its environment witha biologically effective amount of any of the aforesaid compositionswherein the environment is a plant.

This invention also provides a method for controlling an invertebratepest comprising contacting the invertebrate pest or its environment witha biologically effective amount of any of the aforesaid compositionswherein the environment is an animal.

This invention also provides a method for controlling an invertebratepest comprising contacting the invertebrate pest or its environment witha biologically effective amount of any of the aforesaid compositionswherein the environment is a seed.

This invention also provides a method for protecting a seed from aninvertebrate pest comprising contacting the seed with a biologicallyeffective amount of a compound of Formula 1, an N-oxide, or a saltthereof (e.g., as a composition described herein). This invention alsorelates to the treated seed.

This invention further provides a composition for protecting an animalfrom an invertebrate parasitic pest comprising a parasiticidallyeffective amount of a compound of Formula 1, an N-oxide, or a saltthereof, and at least one carrier.

This invention further provides a method for treating, preventing,inhibiting and/or killing ecto and/or endoparasites comprisingadministering to and/or on an animal a parasiticidally effective amountof a compound of Formula 1, an N-oxide, or a salt thereof (e.g., as acomposition described herein). This invention also relates to suchmethod wherein a parasiticidally effective amount of a compound ofFormula 1, an N-oxide, or a salt thereof, (e.g., as a compositiondescribed herein) is administered to an environment (e.g., a stall orblanket) in which an animal resides.

DETAILS OF THE INVENTION

As used herein, the terms “comprises”, “comprising”, “includes”,“including”, “has”, “having”, “contains”, “containing”, “characterizedby” or any other variation thereof, are intended to cover anon-exclusive inclusion, subject to any limitation explicitly indicated.For example, a composition, mixture, process or method that comprises alist of elements is not necessarily limited to only those elements butmay include other elements not expressly listed or inherent to suchcomposition, mixture, process or method.

The transitional phrase “consisting of” excludes any element, step oringredient not specified. If in the claim, such would close the claim tothe inclusion of materials other than those recited except forimpurities ordinarily associated therewith. When the phrase “consistingof” appears in a clause of the body of a claim, rather than immediatelyfollowing the preamble, it limits only the element set forth in thatclause; other elements are not excluded from the claim as a whole.

The transitional phrase “consisting essentially of” is used to define acomposition or method that includes materials, steps, features,components or elements, in addition to those literally disclosed,provided that these additional materials, steps, features, components orelements do not materially affect the basic and novel characteristic(s)of the claimed invention. The term “consisting essentially of” occupiesa middle ground between “comprising” and “consisting of”.

Where applicants have defined an invention or a portion thereof with anopen-ended term such as “comprising”, it should be readily understoodthat (unless otherwise stated) the description should be interpreted toalso describe such an invention using the terms “consisting essentiallyof” or “consisting of”.

Further, unless expressly stated to the contrary, “or” refers to aninclusive or and not to an exclusive or. For example, a condition A or Bis satisfied by any one of the following: A is true (or present) and Bis false (or not present), A is false (or not present) and B is true (orpresent), and both A and B are true (or present).

Also, the indefinite articles “a” and “an” preceding an element orcomponent of the invention are intended to be nonrestrictive regardingthe number of instances (i.e. occurrences) of the element or component.Therefore “a” or “an” should be read to include one or at least one, andthe singular word form of the element or component also includes theplural unless the number is obviously meant to be singular.

As referred to in this disclosure, the term “invertebrate pest” includesarthropods, gastropods and nematodes of economic importance as pests.The term “arthropod” includes insects, mites, spiders, scorpions,centipedes, millipedes, pill bugs and symphylans. The term “gastropod”includes snails, slugs and other Stylommatophora. The term “nematode”refers to a living organism of the Phylum Nematoda. The term “helminths”includes roundworms, heartworms, phytophagous nematodes (Nematoda),flukes (Tematoda), Acanthocephala and tapeworms (Cestoda).

In the context of this disclosure “invertebrate pest control” meansinhibition of invertebrate pest development (including mortality,feeding reduction, and/or mating disruption), and related expressionsare defined analogously.

The term “agronomic” refers to the production of field crops such as forfood and fiber and includes the growth of corn, soybeans and otherlegumes, rice, cereal (e.g., wheat, oats, barley, rye, rice, maize),leafy vegetables (e.g., lettuce, cabbage, and other cole crops),fruiting vegetables (e.g., tomatoes, pepper, eggplant, crucifers andcucurbits), potatoes, sweet potatoes, grapes, cotton, tree fruits (e.g.,pome, stone and citrus), small fruit (berries, cherries) and otherspecialty crops (e.g., canola, sunflower, olives).

The term “nonagronomic” refers to other than field crops, such ashorticultural crops (e.g., greenhouse, nursery or ornamental plants notgrown in a field), residential, agricultural, commercial and industrialstructures, turf (e.g., sod farm, pasture, golf course, lawn, sportsfield, etc.), wood products, stored product, agro-forestry andvegetation management, public health (i.e. human) and animal health(e.g., domesticated animals such as pets, livestock and poultry,undomesticated animals such as wildlife) applications.

Nonagronomic applications include protecting an animal from aninvertebrate parasitic pest by administering a parasiticidally effective(i.e. biologically effective) amount of a compound of the invention,typically in the form of a composition formulated for veterinary use, tothe animal to be protected. As referred to in the present disclosure andclaims, the terms “parasiticidal” and “parasiticidally” refers toobservable effects on an invertebrate parasite pest to provideprotection of an animal from the pest. Parasiticidal effects typicallyrelate to diminishing the occurrence or activity of the targetinvertebrate parasitic pest. Such effects on the pest include necrosis,death, retarded growth, diminished mobility or lessened ability toremain on or in the host animal, reduced feeding and inhibition ofreproduction. These effects on invertebrate parasite pests providecontrol (including prevention, reduction or elimination) of parasiticinfestation or infection of the animal.

In the above recitations, the term “alkyl”, used either alone or incompound words such as “haloalkyl” includes straight-chain or branchedalkyl, such as, methyl, ethyl, n-propyl, i-propyl, or the differentbutyl, pentyl or hexyl isomers. “Alkenyl” includes straight-chain orbranched alkenes such as ethenyl, 1-propenyl, 2-propenyl, and thedifferent butenyl, pentenyl and hexenyl isomers. “Alkenyl” also includespolyenes such as 1,2-propadienyl and 2,4-hexadienyl. “Alkynyl” includesstraight-chain or branched alkynes such as ethynyl, 1-propynyl,2-propynyl and the different butynyl, pentynyl and hexynyl isomers.“Alkynyl” can also include moieties comprised of multiple triple bondssuch as 2,5-hexadiynyl.

“Cycloalkyl” includes, for example, cyclopropyl, cyclobutyl, cyclopentyland cyclohexyl. The term “cycloalkylalkyl” denotes cycloalkylsubstitution on an alkyl moiety. Examples of “cycloalkylalkyl” includecyclopropylmethyl, cyclopentylethyl, and other cycloalkyl moietiesbonded to straight-chain or branched alkyl groups. “Cycloalkenyl”includes groups such as cyclopentenyl and cyclohexenyl as well as groupswith more than one double bond such as 1,3- and 1,4-cyclohexadienyl. Theterm “cycloalkoxy” denotes cycloalkyl attached to and linked through anoxygen atom such as cyclopentyloxy and cyclohexyloxy.“Alkylcycloalkylalkyl” denotes an alkyl group substituted withalkylcycloalkyl. Examples of “alkylcycloalkylalkyl” include 1-, 2-, 3-or 4-methyl or -ethyl cyclohexylmethyl. The term “cycloalkylcycloalkyl”denotes cycloalkyl substitution on another cycloalkyl ring, wherein eachcycloalkyl ring independently has from 3 to 7 carbon atom ring members.Examples of cycloalkylcycloalkyl include cyclopropylcyclopropyl (such as1,1′-bicyclopropyl-1-yl, 1,1′-bicyclopropyl-2-yl), cyclohexylcyclopentyl(such as 4-cyclopentylcyclohexyl) and cyclohexylcyclohexyl (such as1,1′-bicyclohexyl-1-yl), and the different cis- andtrans-cycloalkylcycloalkyl isomers, (such as(1R,2S)-1,1′-bicyclopropyl-2-yl and (1R,2R)-1,1′-bicyclopropyl-2-yl).“Cycloalkylamino” denotes an NH radical substituted with cycloalkyl.Examples of “cycloalkylamino” include cyclopropylamino andcyclohexylamino. The term “cycloalkylaminoalkyl” denotes cycloalkylaminosubstitution on an alkyl group. Examples of “cycloalkylaminoalkyl”include cyclopropylaminomethyl, cyclopentylaminoethyl, and othercycloalkylamino moieties bonded to straight-chain or branched alkylgroups.

The term “halogen”, either alone or in compound words such as“haloalkyl”, or when used in descriptions such as “alkyl substitutedwith halogen” includes fluorine, chlorine, bromine or iodine. Further,when used in compound words such as “haloalkyl”, or when used indescriptions such as “alkyl substituted with halogen” said alkyl may bepartially or fully substituted with halogen atoms which may be the sameor different. Examples of “haloalkyl” or “alkyl substituted withhalogen” include CF₃, CH₂Cl, CH₂CF₃ and CCl₂CF₃. The terms“haloalkenyl”, “haloalkynyl” “haloalkoxy”, “haloalkylthio”,“haloalkylamino”, “haloalkylsulfinyl”, “haloalkylsulfonyl”,“halocycloalkyl”, and the like, are defined analogously to the term“haloalkyl”. Examples of “haloalkenyl” include (Cl)₂C═CHCH₂ andCF₃CH₂CH═CHCH₂. Examples of “haloalkynyl” include HC≡CCHCl, CF₃C≡C,CCl₃C≡C and FCH₂C≡CCH₂. Examples of “haloalkoxy” include CF₃O, CCl₃CH₂O,HCF₂CH₂CH₂O and CF₃CH₂O. Examples of “haloalkylthio” include CCl₃S,CF₃S, CCl₃CH₂S and ClCH₂CH₂CH₂S. Examples of “haloalkylamino” includeCF₃(CH₃)CHNH, (CF₃)₂CHNH and CH₂ClCH₂NH. Examples of “haloalkylsulfinyl”include CF₃S(═O), CCl₃S(═O), CF₃CH₂S(═O) and CF₃CF₂S(═O). Examples of“haloalkylsulfonyl” include CF₃S(═O)₂, CCl₃S(═O)₂, CF₃CH₂S(═O)₂ andCF₃CF₂S(═O)₂. Examples of “halocycloalkyl” include 2-chlorocyclopropyl,2-fluorocyclobutyl, 3-bromocyclopentyl and 4-chlorocyclohexyl. The term“halodialkyl”, either alone or in compound words such as“halodialkylamino”, means at least one of the two alkyl groups issubstituted with at least one halogen atom, and independently eachhalogenated alkyl group may be partially or fully substituted withhalogen atoms which may be the same or different. Examples of“halodialkylamino” include (BrCH₂CH₂)₂N and BrCH₂CH₂(ClCH₂CH₂)N.

“Alkoxy” includes, for example, methoxy, ethoxy, n-propoxy, isopropoxyand the different butoxy, pentoxy and hexyloxy isomers. “Alkoxyalkyl”denotes alkoxy substitution on alkyl. Examples of “alkoxyalkyl” includeCH₂OCH₃, CH₂CH₂OCH₃, CH₂OCH₂CH₃, CH₂OCH₂CH₂CH₂CH₃ and CH₂CH₂OCH₂CH₃.“Alkenyloxy” includes straight-chain or branched alkenyl attached to andlinked through an oxygen atom. Examples of “alkenyloxy” includeH₂C═CHCH₂O, (CH₃)₂C═CHCH₂O, (CH₃)CH═CHCH₂O, (CH₃)CH═C(CH₃)CH₂O andCH₂═CHCH₂CH₂O. “Alkynyloxy” includes straight-chain or branchedalkynyloxy moieties. Examples of “alkynyloxy” include HC≡CCH₂O,CH₃C≡CCH₂O and CH₃C≡CCH₂CH₂O.

The term “alkylthio” includes straight-chain or branched alkylthiomoieties such as methylthio, ethylthio, and the different propylthio,butylthio, pentylthio and hexylthio isomers. “Alkylsulfinyl” includesboth enantiomers of an alkylsulfinyl group. Examples of “alkylsulfinyl”include CH₃S(═O), CH₃CH₂S(═O), CH₃CH₂CH₂S(═O), (CH₃)₂CHS(═O) and thedifferent butylsulfinyl, pentylsulfinyl and hexylsulfinyl isomers.Examples of “alkylsulfonyl” include CH₃S(═O)₂, CH₃CH₂S(═O)₂,CH₃CH₂CH₂S(═O)₂, (CH₃)₂CHS(═O)₂, and the different butylsulfonyl,pentylsulfonyl and hexylsulfonyl isomers. The chemical abbreviationsS(O) and S(═O) as used herein represent a sulfinyl moiety. The chemicalabbreviations SO₂, S(O)₂ and S(═O)₂ as used herein represent a sulfonylmoiety.

“Alkylamino” denotes an NH radical substituted with straight-chain orbranched alkyl. Examples of “alkylamino” include NHCH₂CH₃, NHCH₂CH₂CH₃,and NHCH₂CH(CH₃)₂. “Dialkylamino” denotes an N radical substitutedindependently with two straight-chain or branched alkyl groups. Examplesof “dialkylamino” include N(CH₃)₂, N(CH₃CH₂CH₂)₂ and N(CH₃)CH₂CH₃.“Halodialkylamino” denotes one straight-chain or branched alkyl moietyand one straight-chain or branched haloalkyl moiety bonded to an Nradical, or two independent straight-chain or branched haloalkylmoieties bonded to an N radical, wherein “haloalkyl” is as definedabove. Examples of “halodialkylamino” include N(CH₂CH₃)(CH₂CH₂Cl) andN(CF₂CF₃)₂.

“Alkylcarbonyl” denotes a straight-chain or branched alkyl moiety bondedto a C(O) moiety. The chemical abbreviations C(O) and C(═O) as usedherein represent a carbonyl moiety. Examples of “alkylcarbonyl” includeC(O)CH₃, C(O)CH₂CH₂CH₃ and C(O)CH(CH₃)₂. Examples of “haloalkylcarbonyl”include C(O)CF₃, C(O)CCl₃, C(O)CH₂CF₃ and C(O)CF₂CF₃.

“Alkoxycarbonyl” denotes a straight-chain or branched alkyl moietybonded to a CO₂ moiety. The chemical abbreviations CO₂, C(O)O and C(═O)Oas used herein represent an oxycarbonyl moiety. Examples of“alkoxycarbonyl” include C(O)OCH₃, C(O)OCH₂CH₃, C(O)OCH₂CH₂CH₃ andC(O)OCH(CH₃)₂.

“Alkylaminocarbonyl” denotes a straight-chain or branched alkyl moietybonded to a C(O)NH moiety. The chemical abbreviations C(O)NH, and C(O)Nas used herein represent an amide moiety (i.e. an aminocarbonyl group).Examples of “alkylaminocarbonyl” include C(O)NHCH₃, C(O)NHCH₂CH₂CH₃ andC(O)NHCH(CH₃)₂. “Dialkylaminocarbonyl” denotes two independentstraight-chain or branched alkyl moieties bonded to a C(O)N moiety.Examples of “dialkylaminocarbonyl” include C(O)N(CH₃)₂ andC(O)N(CH₃)(CH₂CH₃).

“Trialkylsilyl” includes 3 branched and/or straight-chain alkyl radicalsattached to and linked through a silicon atom, such as trimethylsilyl,triethylsilyl and tert-butyldimethylsilyl.

“CHO” means formyl, “OCN” means —O—C≡N, and “SCN” means —S—C≡N.

When A is C(R^(3c))═C(R^(3d)), the C(R^(3c))═C(R^(3d)) moiety isoriented so the carbon atom bonded to R^(3d) is connected directly tothe pyrimidinium ring of Formula 1 as shown below.

The total number of carbon atoms in a substituent group is indicated bythe “C_(i)-C_(j)” prefix where i and j are numbers from 1 to 14. Forexample, C₁-C₄ alkyl designates methyl through butyl; C₂ alkoxyalkyldesignates CH₂OCH₃; C₃ alkoxyalkyl designates, for example, CH₃CH(OCH₃),CH₂CH₂OCH₃ or CH₂OCH₂CH₃; and C₄ alkoxyalkyl designates the variousisomers of an alkyl group substituted with an alkoxy group containing atotal of four carbon atoms, examples including CH₂OCH₂CH₂CH₃ andCH₂CH₂OCH₂CH₃.

When a group contains a substituent which can be hydrogen, for exampleR^(3a), then when this substituent is taken as hydrogen, it isrecognized that this is equivalent to said group being unsubstituted.When a variable group is shown to be optionally attached to a position,for example (R^(v))_(r) in U-36 of Exhibit 1 wherein r may be 0, thenhydrogen can be at the position even if not recited in the variablegroup definition. When one or more positions on a group are said to be“not substituted” or “unsubstituted”, then hydrogen atoms are attachedto take up any free valency.

Unless otherwise indicated, a “ring” or “ring system” as a component ofFormula 1 is carbocyclic or heterocyclic. The term “ring system” denotestwo or more connected rings. The term “bicyclic ring system” denotes aring system consisting of two rings sharing two or more common atoms.

A ring or a bicyclic ring system can be part of an extended ring systemcontaining more than two rings wherein substituents on the ring orbicyclic ring system are taken together to form the additional rings,which may be in bicyclic relationships with other rings in the extendedring system.

The term “ring member” refers to an atom (e.g., C, O, N or S) or othermoiety (e.g., C(═O), C(═S) or S(═O)_(u)(═NR²⁴)_(z)) forming the backboneof a ring or ring system. The term “aromatic” indicates that each of thering atoms is essentially in the same plane and has a p-orbitalperpendicular to the ring plane, and that (4n+2) π electrons, where n isa positive integer, are associated with the ring or ring system tocomply with Hückel's rule.

“Partially saturated” and “partially unsaturated” with reference to aring or ring system means that the ring or ring system contains at leastone double bond but the ring or ring system is not aromatic. A ringsystem is aromatic if at least one component ring is aromatic.

The term “carbocyclic ring” denotes a ring wherein the atoms forming thering backbone are selected only from carbon. Unless otherwise indicated,a carbocyclic ring can be a saturated, partially unsaturated, or fullyunsaturated ring. When a fully unsaturated carbocyclic ring satisfiesHückel's rule, then said ring is also called an “aromatic ring”.“Saturated carbocyclic ring” refers to a ring having a backboneconsisting of carbon atoms linked to one another by single bonds; unlessotherwise specified, the remaining carbon valences are occupied byhydrogen atoms.

The terms “heterocyclic ring” or “heterocycle” denotes a ring wherein atleast one of the atoms forming the ring backbone is other than carbon.Unless otherwise indicated, a heterocyclic ring can be a saturated,partially unsaturated, or fully unsaturated ring. “Saturatedheterocyclic ring” refers to a heterocyclic ring containing only singlebonds between ring members. “Partially saturated heterocyclic ring”refers a heterocyclic ring containing at least one double bond but whichis not aromatic. The term “heteroaromatic ring” denotes a fullyunsaturated aromatic ring in which at least one atom forming the ringbackbone is not carbon. Typically a heteroaromatic ring contains no morethan 4 nitrogens, no more than 1 oxygen and no more than 1 sulfur.Unless otherwise indicated, heteroaromatic rings can be attached throughany available carbon or nitrogen by replacement of a hydrogen on saidcarbon or nitrogen. The term “heteroaromatic bicyclic ring system”denotes a ring system consisting of two fused rings, in which at leastone of the two rings is a heteroaromatic ring as defined above.

When a radical (e.g., a 3- to 10-membered ring in the definition of R¹)is optionally substituted with listed substituents with the number ofsubstituents stated (e.g., “up to 5”), then the radical may beunsubstituted or substituted with a number of substituents ranging up tothe high number stated (e.g., “5”), and the attached substituents areindependently selected from the substituents listed.

When a substituent (e.g., R¹) is a ring or ring system, it can beattached to the remainder of Formula 1 through any available ringmember, unless otherwise described.

As noted above, R¹ is, inter alia, a 3- to 10-membered ring or a 7- to11-membered ring system, each ring or ring system containing ringmembers selected from carbon atoms and up to 4 heteroatoms independentlyselected from up to 2 O, up to 2 S, and up to 4 N, wherein up to 3carbon atom ring members are independently selected from C(═O) and C(═S)and the sulfur atom ring members are independently selected fromS(═O)_(u)(═NR²⁴)_(z), each ring or ring system optionally substitutedwith up to 5 substituents independently selected from R¹⁴. In thisdefinition the ring members selected from up to 2 O, up to 2 S and up to4 N are optional, because the number of heteroatom ring members may bezero. When no heteroatom ring members are present, the ring or ringsystem is carbocyclic. If at least one heteroatom ring member ispresent, the ring or ring system is heterocyclic. The definition ofS(═O)_(u)(═NR²⁴)_(z) allows up to 2 sulfur ring members, which can beoxidized sulfur moieties (e.g., S(═O) or S(═O)₂) or unoxidized sulfuratoms (i.e. when u and z are both zero). The nitrogen atom ring membersmay be oxidized as N-oxides, because compounds relating to Formula 1also include N-oxide derivatives. The up to 3 carbon atom ring membersselected from C(═O) and C(═S) are in addition to the up to 4 heteroatomsselected from up to 2 O, up to 2 S and up to 4 N atoms. As the R¹⁴substituents are optional, 0 to 5 substituents may be present, limitedonly by the number of available points of attachment.

The term “unsubstituted” in connection with a group such as a ring orring system means the group does not have any substituents other thanits one or more attachments to the remainder of Formula 1. The term“optionally substituted” means that the number of substituents can bezero. Unless otherwise indicated, optionally substituted groups may besubstituted with as many optional substituents as can be accommodated byreplacing a hydrogen atom with a non-hydrogen substituent on anyavailable carbon or nitrogen atom. Commonly, the number of optionalsubstituents (when present) ranges from 1 to 3.

The number of optional substituents may be restricted by an expressedlimitation. For example, the phrase “optionally substituted with up to 5substituents independently selected from R¹⁵” means that 0, 1, 2, 3, 4or 5 substituents can be present (if the number of potential connectionpoints allows). When a range specified for the number of substituentsexceeds the number of positions available for substituents on a ring,the actual higher end of the range is recognized to be the number ofavailable positions.

When the number of optional substituents is not restricted by anexpressed limitation (e.g., the phrases “optionally substituted withhalogen” or “unsubstituted or substituted with at least one substituentindependently selected from”), it is understood to mean that the numberof optional substituents can range from 0 up to the number of positionsavailable. One skilled in the art will appreciate that while somesubstituents such as halogen can be present at every available position(for example, the C₂F₅ substituent is a C₂ alkyl group substituted withthe maximum number of 5 fluorine atoms), practical factors such as costand synthetic accessibility can limit the number of occurrences of othersubstituents. These limitations are part of the general syntheticknowledge known to those skilled in the art. Of note are embodimentswherein in the absence of expressed limitation of number of optionalsubstituents, the number of optional substituents is up to 3 (i.e. 0, 1,2 or 3) if accommodated by the number of available positions.

As noted above, substituents such as R¹ can be (among others) a 5- or6-membered heteroaromatic ring, optionally substituted with one or moresubstituents selected from a group of substituents as defined in theSummary of Invention. Examples of a 5- or 6-membered heteroaromatic ringoptionally substituted with one or more substituents include the ringsU-2 through U-61 illustrated in Exhibit 1 wherein R^(v) is anysubstituent as defined in the Summary of the Invention (e.g., for R¹)and r is an integer from 0 to 5, limited by the number of availablepositions on each U group. As U-29, U-30, U-36, U-37, U-38, U-39, U-40,U-41, U-42 and U-43 have only one available position, for these U groupsr is limited to the integers 0 or 1, and r being 0 means that the Ugroup is unsubstituted and a hydrogen is present at the positionindicated by (R^(v))_(r).

As noted above, substituents such as R¹ can be (among others) an 8-, 9-or 10-membered heteroaromatic bicyclic ring system optionallysubstituted with up to 5 substituents selected from a group ofsubstituents as defined in the Summary of Invention. Examples of an 8-,9- or 10-membered heteroaromatic bicyclic ring system optionallysubstituted with up to 5 substituents include the ring systems H-1through H-23 illustrated in Exhibit 2 wherein R^(v) is any substituentas defined in the Summary of the Invention (e.g., for R¹) and r is aninteger from 0 to 5, limited by the number of available positions oneach H group.

Although R^(v) groups are shown in the structures U-1 through U-61 andH-1 through H-23, it is noted that they do not need to be present sincethey are optional substituents. The nitrogen atoms that requiresubstitution to fill their valence are substituted with H or R^(v). Notethat when the attachment point between (R^(v))_(r) and the U or H groupis illustrated as floating, (R^(v))_(r) can be attached to any availablecarbon atom or nitrogen atom of the U or H group. Note that when theattachment point on the U or H group is illustrated as floating, the Uor H group can be attached to the remainder of Formula 1 through anyavailable carbon or nitrogen of the U or H group by replacement of ahydrogen atom.

A wide variety of synthetic methods are known in the art to enablepreparation of aromatic and nonaromatic heterocyclic rings and ringsystems; for extensive reviews see the eight volume set of ComprehensiveHeterocyclic Chemistry, A. R. Katritzky and C. W. Rees editors-in-chief,Pergamon Press, Oxford, 1984 and the twelve volume set of ComprehensiveHeterocyclic Chemistry II, A. R. Katritzky, C. W. Rees and E. F. V.Scriven editors-in-chief, Pergamon Press, Oxford, 1996.

The compounds of Formula 1 are mesoionic inner salts. “Inner salts”,also known in the art as “zwitterions”, are electrically neutralmolecules but carry formal positive and negative charges on differentatoms in each valence bond structure according to valence bond theory.Furthermore the molecular structure of the compounds of Formula 1 can berepresented by the six valence bond structures shown below, each placingthe formal positive and negative charges on different atoms. Because ofthis resonance, the compounds of Formula 1 are also described as“mesoionic”. Although for sake of simplicity, the molecular structure ofFormula 1 is depicted as a single valence bond structure herein, thisparticular valence bond structure is to be understood as representativeof all six valence bond structures relevant to bonding in molecules ofcompounds of Formula 1. Therefore reference to Formula 1 herein relatesto all six applicable valence bond structures and other (e.g., molecularorbital theory) structures unless otherwise specified.

Compounds of this invention can exist as one or more stereoisomers. Thevarious stereoisomers include enantiomers, diastereomers, atropisomersand geometric isomers. One skilled in the art will appreciate that onestereoisomer may be more active and/or may exhibit beneficial effectswhen enriched relative to the other stereoisomer(s) or when separatedfrom the other stereoisomer(s). Additionally, the skilled artisan knowshow to separate, enrich, and/or to selectively prepare saidstereoisomers. The compounds of the invention may be present as amixture of stereoisomers, individual stereoisomers or as an opticallyactive form.

Compounds of this invention can exist as one or more conformationalisomers due to restricted bond rotation caused by steric hinderance. Forexample, a compound of Formula 1 wherein Z is a direct bond and R¹ isphenyl substituted in the ortho-position with a sterically demandingalkyl group (e.g., isopropyl) may exist as two rotamers due torestricted rotation about the R¹-pyrimidinium ring bond. This inventioncomprises mixtures of conformational isomers. In addition, thisinvention includes compounds that are enriched in one conformer relativeto others.

Compounds selected from Formula 1 (including all stereoisomers,N-oxides, and salts thereof) typically exist in more than one form, andFormula 1 thus includes all crystalline and non-crystalline forms of thecompounds that Formula 1 represents. Non-crystalline forms includeembodiments which are solids such as waxes and gums as well asembodiments which are liquids such as solutions and melts. Crystallineforms include embodiments which represent essentially a single crystaltype and embodiments which represent a mixture of polymorphs (i.e.different crystalline types). The term “polymorph” refers to aparticular crystalline form of a chemical compound that can crystallizein different crystalline forms, these forms having differentarrangements and/or conformations of the molecules in the crystallattice. Although polymorphs can have the same chemical composition,they can also differ in composition due to the presence or absence ofco-crystallized water or other molecules, which can be weakly orstrongly bound in the lattice. Polymorphs can differ in such chemical,physical and biological properties as crystal shape, density, hardness,color, chemical stability, melting point, hygroscopicity,suspensibility, dissolution rate and biological availability. Oneskilled in the art will appreciate that a polymorph of a compoundrepresented by Formula 1 can exhibit beneficial effects (e.g.,suitability for preparation of useful formulations, improved biologicalperformance) relative to another polymorph or a mixture of polymorphs ofthe same compound represented by Formula 1. Preparation and isolation ofa particular polymorph of a compound represented by Formula 1 can beachieved by methods known to those skilled in the art including, forexample, crystallization using selected solvents and temperatures.

One skilled in the art will appreciate that not all nitrogen-containingheterocycles can form N-oxides since the nitrogen requires an availablelone pair for oxidation to the oxide; one skilled in the art willrecognize those nitrogen-containing heterocycles which can formN-oxides. One skilled in the art will also recognize that tertiaryamines can form N-oxides. Synthetic methods for the preparation ofN-oxides of heterocycles and tertiary amines are very well known by oneskilled in the art including the oxidation of heterocycles and tertiaryamines with peroxy acids such as peracetic and 3-chloroperbenzoic acid(MCPBA), hydrogen peroxide, alkyl hydroperoxides such as t-butylhydroperoxide, sodium perborate, and dioxiranes such asdimethyldioxirane. These methods for the preparation of N-oxides havebeen extensively described and reviewed in the literature, see forexample: T. L. Gilchrist in Comprehensive Organic Synthesis, vol. 7, pp748-750, S. V. Ley, Ed., Pergamon Press; M. Tisler and B. Stanovnik inComprehensive Heterocyclic Chemistry, vol. 3, pp 18-20, A. J. Boultonand A. McKillop, Eds., Pergamon Press; M. R. Grimmett and B. R. T. Keenein Advances in Heterocyclic Chemistry, vol. 43, pp 149-161, A. R.Katritzky, Ed., Academic Press; M. Tisler and B. Stanovnik in Advancesin Heterocyclic Chemistry, vol. 9, pp 285-291, A. R. Katritzky and A. J.Boulton, Eds., Academic Press; and G. W. H. Cheeseman and E. S. G.Werstiuk in Advances in Heterocyclic Chemistry, vol. 22, pp 390-392, A.R. Katritzky and A. J. Boulton, Eds., Academic Press.

One skilled in the art recognizes that because in the environment andunder physiological conditions salts of chemical compounds are inequilibrium with their corresponding nonsalt forms, salts share thebiological utility of the nonsalt forms. Thus a wide variety of salts ofthe compounds of Formula 1 are useful for control of invertebrate pestsand animal parasites (i.e. are suitable for animal health use). Thesalts of the compounds of Formula 1 include acid-addition salts withinorganic or organic acids such as hydrobromic, hydrochloric, nitric,phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic,oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valericacids. When a compound of Formula 1 contains an acidic moiety such as acarboxylic acid or phenol, salts also include those formed with organicor inorganic bases such as pyridine, triethylamine or ammonia, oramides, hydrides, hydroxides or carbonates of sodium, potassium,lithium, calcium, magnesium or barium. Accordingly, the presentinvention comprises compounds selected from Formula 1, N-oxides, andsalts thereof.

Embodiments of the present invention as described in the Summary of theInvention include those described below. In the following EmbodimentsFormula 1 includes stereoisomers, N-oxides, and salts thereof, andreference to “a compound of Formula 1” includes the definitions ofsubstituents specified in the Summary of the Invention unless furtherdefined in the Embodiments.

In the Embodiments that follow, recitation of the word “independently”before more than one variable being defined means that the definitioncan be applied to each variable independently of the other variables.For example, an Embodiment reciting “independently R^(3a), R^(3b) whentaken alone, and R^(3c) when taken alone are H or halogen” is equivalentto three Embodiments reciting: “R^(3a) is H or halogen”, “R^(3b) whentaken alone is H or halogen”, and “R^(3c) when taken alone is H orhalogen”, each of which can be independently used as basis to amend oradd claims.

Embodiment 1

A compound of Formula 1 wherein X is O.

Embodiment 2

A compound of Formula 1 wherein X is S.

Embodiment 3

A compound of Formula 1 or Embodiments 1 or 2 wherein Y is O.

Embodiment 4

A compound of Formula 1 or Embodiments 1 or 2 wherein Y is S.

Embodiment 5

A compound of Formula 1 or any one of Embodiments 1-4 wherein A is S,NR^(3e) or C(R^(3c))═C(R^(3d)).

Embodiment 5a

A compound of Embodiment 5 wherein A is S or C(R^(3c))═C(R^(3d)).

Embodiment 5b

A compound of Embodiment 5a wherein A is C(R^(3c)═C(R^(3d)).

Embodiment 5c

A compound of Embodiment 5a wherein A is S.

Embodiment 5d

A compound of Embodiment 5 wherein A is C(R^(3c))═C(R^(3d)) or NR^(3e);

Embodiment 5e

A compound of Embodiment 5d wherein A is NR^(3e).

Embodiment 6

A compound of Formula 1 or any one of Embodiments 1-5b whereinindependently R^(3a) when taken alone (i.e. when R^(3a) is not takentogether with R^(3b) to form a ring), R^(3b) when taken alone (i.e. whenR^(3b) is not taken together with R^(3a), R^(3c) or R^(3e) to form aring), R^(3c) when taken alone (i.e. when R^(3c) is not taken togetherwith R^(3b) or R^(3d) to form a ring) and R^(3d) when taken alone (i.e.when R^(3d) is not taken together with R^(3c) to form a ring) are H,halogen, cyano, hydroxy, amino, nitro, SF₅, OCN, SCN, CHO, C(═O)OH,C(═O)NH₂, C(═S)NH₂, SO₂NH₂, C(═O)R¹⁸, C(═O)OR¹⁸, NHR¹⁸, NR¹⁸R¹⁹,C(═O)NR²¹R¹⁹, C(═S)NR²¹R¹⁹, SO₂NR²¹R¹⁹, OC(═O)R²¹, OC(═O)OR¹⁸,OC(═O)NR²¹R¹⁹, N(R²¹)C(═O)R²¹, N(R²¹)C(═O)OR¹⁹, N(R²¹)C(═O)NR²¹R²²,OSO₂R¹⁸, OSO₂NR²¹R²², NR²¹SO₂R¹⁸, NR²¹SO₂NR²¹R²², Si(R¹⁸R¹⁹R²⁰) orZ¹Q^(t); or C₁-C₈ alkyl, C₂-C₈ alkenyl, C₂-C₈ alkynyl, C₃-C₁₀cycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₆-C₁₄cycloalkylcycloalkyl, C₅-C₁₀ alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl,C₁-C₈ alkoxy, C₃-C₈ cycloalkoxy, C₄-C₁₀ cycloalkylalkoxy, C₂-C₈alkenyloxy, C₂-C₈ alkynyloxy, C₁-C₈ alkylthio, C₁-C₈ alkylsulfinyl,C₁-C₈ alkylsulfonyl, C₃-C₈ cycloalkylthio, C₃-C₈ cycloalkylsulfinyl,C₃-C₈ cycloalkylsulfonyl, C₄-C₁₀ cycloalkylalkylthio, C₄-C₁₀cycloalkylalkylsulfinyl, C₄-C₁₀ cycloalkylalkylsulfonyl, C₂-C₈alkenylthio, C₂-C₈ alkenylsulfinyl, C₂-C₈ alkenylsulfonyl, C₂-C₈alkynylthio, C₂-C₈ alkynylsulfinyl or C₂-C₈ alkynylsulfonyl, eachunsubstituted or substituted with at least one substituent independentlyselected from R¹⁷.

Embodiment 6a

A compound of Embodiment 6 wherein independently R^(3a) when takenalone, R^(3b) when taken alone, R^(3c) when taken alone and R^(3d) whentaken alone are H, halogen, cyano, OCN, SCN, CHO, SO₂NH₂, C(═O)R¹⁸,C(═O)OR¹⁸, C(═O)NR²¹R¹⁹, C(═S)NR²¹R¹⁹, SO₂NR²¹R¹⁹, OC(═O)R²¹,OC(═O)OR¹⁸, OC(═O)NR²¹R¹⁹ or Z¹Q^(t); or C₁-C₈ alkyl, C₂-C₈ alkenyl,C₂-C₈ alkynyl, C₃-C₁₀ cycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀cycloalkylalkyl, C₆-C₁₄ cycloalkylcycloalkyl, C₅-C₁₀alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl, C₁-C₈ alkoxy, C₃-C₈cycloalkoxy, C₄-C₁₀ cycloalkylalkoxy, C₂-C₈ alkenyloxy, C₂-C₈alkynyloxy, C₁-C₈ alkylthio, C₃-C₈ cycloalkylthio, C₄-C₁₀cycloalkylalkylthio, C₄-C₁₀ cycloalkylalkylsulfinyl, C₄-C₁₀cycloalkylalkylsulfonyl, C₂-C₈ alkenylthio or C₂-C₈ alkynylthio, eachunsubstituted or substituted with at least one substituent independentlyselected from R¹⁷.

Embodiment 6b

A compound of Embodiment 6a wherein independently R^(3a) when takenalone, R^(3b) when taken alone, R^(3c) when taken alone and R^(3d) whentaken alone are H or halogen; or C₁-C₈ alkyl, C₂-C₈ alkenyl, C₂-C₈alkynyl, C₃-C₁₀ cycloalkyl, C₁-C₈ alkoxy, C₃-C₈ cycloalkoxy, C₂-C₈alkenyloxy or C₂-C₈ alkynyloxy, each unsubstituted or substituted withat least one substituent independently selected from R¹⁷.

Embodiment 6c

A compound of Embodiment 6b wherein independently R^(3a) when takenalone, R^(3b) when taken alone, R^(3c) when taken alone and R^(3d) whentaken alone are H or halogen; or C₁-C₈ alkyl, C₃-C₁₀ cycloalkyl or C₁-C₈alkoxy, each optionally substituted with halogen.

Embodiment 6d

A compound of Embodiment 6c wherein independently R^(3a) when takenalone, R^(3b) when taken alone, and R^(3c) when taken alone are H orhalogen.

Embodiment 6e

A compound of Embodiment 6d wherein independently R^(3a) when takenalone, R^(3b) when taken alone and R^(3c) when taken alone are H.

Embodiment 7

A compound of Formula 1 or any one of Embodiments 1-6e wherein R^(3d)when taken alone is H, halogen, C₁-C₈ alkyl or C₁-C₈ alkoxy.

Embodiment 7a

A compound of Embodiment 7 wherein R^(3d) when taken alone is halogen,C₁-C₈ alkyl or C₁-C₈ alkoxy.

Embodiment 7a1

A compound of Formula 1 or any one of Embodiments 1-6e wherein R^(3d)when taken alone is halogen, C₁-C₈ alkyl, C₁-C₈ alkoxy, C₁-C₈ haloalkylor C₁-C₈ haloalkoxy.

Embodiment 7b

A compound of Embodiment 7a wherein R^(3d) when taken alone is halogen,C₁-C₄ alkyl or C₁-C₄ alkoxy.

Embodiment 7c

A compound of Embodiment 7b wherein R^(3d) when taken alone is F, Cl,Br, CH₃ or OCH₃.

Embodiment 7d

A compound of Embodiment 7c wherein R^(3d) when taken alone is CH₃.

Embodiment 7e

A compound of Embodiment 7 wherein R^(3d) when taken alone is H,halogen, C₁-C₄ alkyl or C₁-C₄ alkoxy.

Embodiment 7f

A compound of Embodiment 7e wherein R^(3d) when taken alone is H orhalogen.

Embodiment 7g

A compound of Embodiment 7e wherein R^(3d) when taken alone is H, F, Cl,Br, CH₃ or OCH₃.

Embodiment 8

A compound of Formula 1 or any one of Embodiments 1-7g wherein R^(3c)and R^(3d) are taken alone.

Embodiment 9

A compound of Formula 1 or any one of Embodiments 1-7g wherein whenR^(3c) and R^(3d) are taken together with the adjacent carbon atoms towhich they are attached to form a 5- or 6-membered ring (which isunderstood to be optionally substituted with the substituents describedin the Summary of the Invention).

Embodiment 9a

A compound of Embodiment 9 wherein the 5- or 6-membered ring formed isaromatic.

Embodiment 9b

A compound of Embodiment 9a wherein the 5- or 6-membered ring formed is6-membered and carbocyclic (i.e. a fused benzene ring optionallysubstituted as described in Embodiment 9).

Embodiment 9d

A compound of Embodiment 9 wherein the 5- or 6-membered ring formed ispartially unsaturated (and carbocyclic or heterocyclic).

Embodiment 9e

A compound of Formula 1 or any one of Embodiments 1-7g and 9-9d whereinR^(3c) and R^(3d) are taken together with the carbon atoms to which theyare attached to form a ring (which is optionally substituted asdescribed in Embodiment 9).

Embodiment 10

A compound of Formula 1 or any one of Embodiments 1-9d wherein R^(3e)when taken alone (i.e. when R^(3e) is not taken together with R^(3b) toform a ring) is H, hydroxy, amino, CHO, C(═O)NH₂, C(═S)NH₂, SO₂NH₂,C(═O)R¹⁸, C(═O)OR¹⁸, NHR¹⁸, NR¹⁸R¹⁹, C(═O)NR²¹R¹⁹, C(═S)NR²¹R¹⁹,SO₂NR²¹R¹⁹, OC(═O)R²¹, OC(═O)OR¹⁸, OC(═O)NR²¹R¹⁹, N(R²¹)C(═O)R²¹,N(R²¹)C(═O)OR¹⁹, N(R²¹)C(═O)NR²¹R²², OSO₂R¹⁸, OSO₂NR²¹R²², NR²¹SO₂R¹⁸,NR²¹SO₂NR²¹R²², Si(R¹⁸R¹⁹R²⁰) or Z¹Q^(t); or C₁-C₈ alkyl, C₂-C₈ alkenyl,C₂-C₈ alkynyl, C₃-C₁₀ cycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀cycloalkylalkyl, C₆-C₁₄ cycloalkylcycloalkyl, C₅-C₁₀alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl, C₁-C₈ alkoxy, C₃-C₈cycloalkoxy, C₄-C₁₀ cycloalkylalkoxy, C₂-C₈ alkenyloxy or C₂-C₈alkynyloxy, each unsubstituted or substituted with at least onesubstituent independently selected from R¹⁷.

Embodiment 10a

A compound of Embodiment 10 wherein R^(3e) when taken alone is H, CHO,C(═O)R¹⁸, C(═O)OR¹⁸, C(═O)NR²¹R¹⁹, C(═S)NR²¹R¹⁹, SO₂NR²¹R¹⁹, C₁-C₈alkyl, C₃-C₈ cycloalkyl or C₁-C₈ alkoxy.

Embodiment 10b

A compound of Embodiment 10a wherein R^(3e) when taken alone is H, C₁-C₄alkyl, C₃-C₄ cycloalkyl or C₁-C₄ alkoxy.

Embodiment 10c

A compound of Embodiment 10b wherein R^(3e) when taken alone is H orC₁-C₄ alkyl.

Embodiment 10d

A compound of Embodiment 10c wherein R^(3e) when taken alone is C₁-C₄alkyl.

Embodiment 10e

A compound of Embodiment 10d wherein R^(3e) when taken alone is CH₃.

Embodiment 10f

A compound of Embodiment 10c wherein R^(3e) when taken alone is H orCH₃.

Embodiment 10g

A compound of Embodiment 10f wherein R^(3e) when taken alone is H.

Embodiment 11

A compound of Formula 1 or any one of Embodiments 1-10 wherein instancesof R¹⁷ in the definition of R^(3e) are independently selected fromR^(17a); R^(17a) is halogen, OR¹¹ or Z^(1a)Q^(t); and Z^(1a) is a directbond.

Embodiment 12

A compound of Formula 1 or any one of Embodiments 1-11 wherein R^(3b)and R^(3e) are taken alone (i.e. R^(3b) and R^(3e) are not takentogether to form a ring).

Embodiment 13

A compound of Formula 1 or any one of Embodiments 1-11 wherein whenR^(3e) and R^(3b) are taken together with the adjacent carbon atoms towhich they are attached to form a 5- or 6-membered ring (which isunderstood to be optionally substituted with the substituents describedin the Summary of the Invention).

Embodiment 14

A compound of Embodiment 13 wherein the 5- or 6-membered ring formed isa fused pyridine ring (which is optionally substituted as described inEmbodiment 13).

Embodiment 15

A compound of Formula 1 or any one of Embodiments 1-14 wherein Z is adirect bond, O, NR⁶, C(═X¹), C(═X¹)E, EC(═X¹), C(═NOR⁸) or C(═NN(R⁶)₂).

Embodiment 15a

A compound of Embodiment 15 wherein Z is a direct bond, C(═X¹), C(═X¹)E,EC(═X¹), C(═NOR⁸) or C(═NN(R⁶)₂).

Embodiment 15b

A compound of Embodiment 15a wherein Z is a direct bond, C(═X¹) orC(═X¹)E.

Embodiment 15c

A compound of Embodiment 15b wherein Z is C(═X¹)E.

Embodiment 15d

A compound of Embodiment 15b wherein Z is C(═X¹).

Embodiment 15e

A compound of Embodiment 15b wherein Z is a direct bond.

Embodiment 16

A compound of Formula 1 or any one of Embodiments 1-15d wherein X¹ is Oor S.

Embodiment 16a

A compound of Formula 1 or any one of Embodiments 1-15d wherein X¹ isNR⁹.

Embodiment 16b

A compound of Embodiment 16 wherein X¹ is O.

Embodiment 16c

A compound of Embodiment 16 wherein X¹ is S.

Embodiment 17

A compound of Formula 1 or any one of Embodiments 1-15c wherein E is O.

Embodiment 17a

A compound of Formula 1 or any one of Embodiments 1-15c wherein E is S.

Embodiment 17b

A compound of Formula 1 or any one of Embodiments 1-15c wherein E isNR^(9a).

Embodiment 18

A compound of Formula 1 or any one of Embodiments 1-15d and 16a whereineach R⁹ is independently C₁-C₆ alkyl, C₂-C₆ alkylcarbonyl or C₂-C₆alkoxycarbonyl.

Embodiment 18a

A compound of Embodiment 18 wherein each R⁹ is independently CH₃,C(═O)CH₃ or C(═O)OCH₃.

Embodiment 19

A compound of Formula 1 or any one of Embodiments 1-15c, 16-16c and 17bwherein each R^(9a) is independently H, C₁-C₆ alkyl, C₂-C₆ alkylcarbonylor C₂-C₆ alkoxycarbonyl.

Embodiment 19a

A compound of Embodiment 19 wherein each R^(9a) is independently H, CH₃,C(═O)CH₃ or C(═O)OCH₃.

Embodiment 20

A compound of Formula 1 or any one of Embodiments 1-19a wherein R¹ is H,halogen, cyano, CHO, C(═O)OH, C(═O)NH₂ or C(═S)NH₂; or C₁-C₈ alkyl,C₂-C₈ alkenyl, C₂-C₈ alkynyl, C₃-C₁₀ cycloalkyl, C₄-C₁₀ alkylcycloalkyl,C₄-C₁₀ cycloalkylalkyl, C₆-C₁₄ cycloalkylcycloalkyl, C₅-C₁₀alkylcycloalkylalkyl or C₃-C₆ cycloalkenyl, each unsubstituted orsubstituted with at least one substituent independently selected fromthe group consisting of halogen, cyano, nitro, CHO, C(═O)OH, C(═O)NH₂,C(═O)R¹⁰, C(═O)OR¹¹, C(═O)NR¹²R¹³, OR¹¹, S(O)_(n)R¹⁰, SO₂NR¹²R¹³,Si(R¹⁰)₃ and Z¹Q^(t); or a 3- to 10-membered ring or a 7- to 11-memberedring system, each ring or ring system containing ring members selectedfrom carbon atoms and up to 4 heteroatoms independently selected from upto 2 O, up to 2 S, and up to 4 N, wherein up to 3 carbon atom ringmembers are independently selected from C(═O) and C(═S) and the sulfuratom ring members are independently selected from S(═O)_(u)(═NR²⁴)_(z),each ring or ring system optionally substituted with up to 5substituents independently selected from R¹⁴.

Embodiment 20a

A compound of Embodiment 20 wherein R¹ is H, halogen, cyano or CHO; orC₁-C₈ alkyl, C₂-C₈ alkenyl, C₂-C₈ alkynyl or C₃-C₆ cycloalkenyl, eachunsubstituted or substituted with at least one substituent independentlyselected from the group consisting of halogen, cyano, nitro, CHO,C(═O)OH, C(═O)NH₂, C(═O)R¹⁰, C(═O)OR¹¹, C(═O)NR¹²R¹³, OR¹¹, S(O)_(n)R¹⁰,SO₂NR¹²R¹³, Si(R¹⁰)₃ and Z¹Q^(t); or a 3- to 10-membered ring or a 7- to11-membered ring system, each ring or ring system containing ringmembers selected from carbon atoms and up to 4 heteroatoms independentlyselected from up to 2 O, up to 2 S, and up to 4 N, wherein up to 3carbon atom ring members are independently selected from C(═O) and C(═S)and the sulfur atom ring members are independently selected fromS(═O)_(u)(═NR²⁴)_(z), each ring or ring system optionally substitutedwith up to 5 substituents independently selected from R¹⁴.

Embodiment 20b

A compound of Embodiment 20a wherein R¹ is H, halogen or CHO; or C₁-C₈alkyl unsubstituted or substituted with at least one substituentindependently selected from the group consisting of halogen and Z¹Q^(t);or C₂-C₈ alkenyl or C₂-C₈ alkynyl, each unsubstituted or substitutedwith at least one substituent independently selected from the groupconsisting of halogen, cyano, nitro, CHO, C(═O)OH, C(═O)NH₂, C(═O)R¹⁰,C(═O)OR¹¹, C(═O)NR¹²R¹³, OR¹¹, S(O)_(n)R¹⁰, SO₂NR¹²R¹³, Si(R¹⁰)₃ andZ¹Q^(t); or a 3- to 10-membered ring or a 7- to 11-membered ring system,each ring or ring system containing ring members selected from carbonatoms and up to 4 heteroatoms independently selected from up to 2 O, upto 2 S, and up to 4 N, wherein up to 3 carbon atom ring members areindependently selected from C(═O) and C(═S) and the sulfur atom ringmembers are independently selected from S(═O)_(u)(═NR²⁴)_(z), each ringor ring system optionally substituted with up to 5 substituentsindependently selected from R¹⁴.

Embodiment 20c

A compound of Formula 1 or any one of Embodiments 1-20b whereininstances of Z¹Q^(t) in the definition of R¹ are independently selectedfrom Z^(1b)Q^(tb); wherein Z^(1b) is a direct bond; and Q^(tb) is a 5-or 6-membered carbocyclic or heterocyclic ring unsubstituted orsubstituted with at least one substituent independently selected fromthe group consisting of halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₄alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ haloalkylthio, C₁-C₄alkylsulfinyl and C₁-C₄ haloalkylsulfinyl.

Embodiment 21

A compound of Embodiment 20b wherein R¹ is C₁-C₈ alkyl optionallysubstituted with halogen; or a 3- to 10-membered ring or a 7- to11-membered ring system, each ring or ring system containing ringmembers selected from carbon atoms and up to 4 heteroatoms independentlyselected from up to 2 O, up to 2 S, and up to 4 N, wherein up to 3carbon atom ring members are independently selected from C(═O) and C(═S)and the sulfur atom ring members are independently selected fromS(═O)_(u)(═NR²⁴)_(z), each ring or ring system optionally substitutedwith up to 5 substituents independently selected from R¹⁴.

Embodiment 21a

A compound of Embodiment 21 wherein R¹ is a 3- to 10-membered ring or a7- to 11-membered ring system, each ring or ring system containing ringmembers selected from carbon atoms and up to 4 heteroatoms independentlyselected from up to 2 O, up to 2 S, and up to 4 N, wherein up to 3carbon atom ring members are independently selected from C(═O) and C(═S)and the sulfur atom ring members are independently selected fromS(═O)_(u)(═NR²⁴)_(z), each ring or ring system optionally substitutedwith up to 5 substituents independently selected from R¹⁴.

Embodiment 21b

A compound of Formula 1 or any one of Embodiments 1-21a wherein the ringor ring system of R¹ is partially unsaturated or aromatic (includingheteroaromatic).

Embodiment 21c

A compound of Embodiment 21b wherein the ring or ring system of R¹ isaromatic (including heteroaromatic).

Embodiment 21d

A compound of Formula 1 or any one of Embodiments 1-21c wherein the ringsystem of R¹ is bicyclic.

Embodiment 22

A compound of Formula 1 or any one of Embodiments 1-21c wherein R¹ is a3- to 10-membered ring containing ring members selected from carbonatoms and up to 4 heteroatoms independently selected from up to 2 O, upto 2 S, and up to 4 N, wherein up to 3 carbon atom ring members areindependently selected from C(═O) and C(═S) and the sulfur atom ringmembers are independently selected from S(═O)_(u)(═NR²⁴)_(z), andoptionally substituted with up to 5 substituents independently selectedfrom R¹⁴.

Embodiment 22a

A compound of Embodiment 22 wherein the ring of R¹ is 5- or 6-membered.

Embodiment 22b

A compound of Embodiment 22 or 22a wherein the ring of R¹ iscarbocyclic.

Embodiment 22c

A compound of Embodiment 22 or 22a wherein the ring of R¹ isheterocyclic.

Embodiment 22d

A compound of Embodiment 22a wherein the ring is phenyl optionallysubstituted with up to 5 substituents independently selected from R¹⁴; a5-membered heterocyclic ring optionally substituted with up to 3substituents independently selected from R¹⁴; or a 6-memberedheterocyclic ring optionally substituted with up to 5 substituentsindependently selected from R¹⁴.

Embodiment 22e

A compound of Embodiment 22d wherein R¹ is phenyl optionally substitutedwith up to 5 substituents independently selected from R¹⁴; or pyridinyloptionally substituted with up to 4 substituents independently selectedfrom R¹⁴.

Embodiment 22f

A compound of Embodiment 22e wherein R¹ is phenyl optionally substitutedwith up to 3 substituents independently selected from R¹⁴; or pyridinyloptionally substituted with up to 2 substituents independently selectedfrom R¹⁴.

Embodiment 22g

A compound of Embodiment 22f wherein R¹ is phenyl optionally substitutedwith up to 3 substituents independently selected from R¹⁴.

Embodiment 22h

A compound of Embodiment 22f wherein R¹ is pyridinyl optionallysubstituted with up to 2 substituents independently selected from R¹⁴.

Embodiment 22i

A compound of Formula 1 or any one of Embodiments 1-22h wherein

-   -   R¹⁴ when taken alone (i.e. when not taken together with another        instance of R¹⁴ on an adjacent ring atom to form a ring) is        halogen, cyano, SF₅, CHO, C(═O)R¹⁸, C(═O)OR¹⁸, C(═O)NR²¹R¹⁹,        Z¹Q^(t) or Z¹Q^(i)Z¹Q^(t); or C₁-C₈ alkyl, C₂-C₈ alkenyl, C₂-C₈        alkynyl, C₃-C₁₀ cycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀        cycloalkylalkyl, C₁-C₈ alkoxy, C₃-C₈ cycloalkoxy, C₄-C₁₀        cycloalkylalkoxy, C₂-C₈ alkenyloxy, C₂-C₈ alkynyloxy, C₁-C₈        alkylthio, C₁-C₈ alkylsulfinyl, C₁-C₈ alkylsulfonyl, C₃-C₈        cycloalkylthio, C₄-C₁₀ cycloalkylalkylthio, C₂-C₈ alkenylthio,        C₂-C₈ alkynylthio, each unsubstituted or substituted with at        least one substituent independently selected from R^(17a); and        R^(17a) is halogen, OR¹¹ or Z¹Q^(t).

Embodiment 22j

A compound of Embodiment 22i wherein R¹⁴ when taken alone is halogen orZ¹Q^(t); or C₁-C₈ alkyl, C₁-C₈ alkoxy or C₁-C₈ alkylthio, eachoptionally substituted with halogen.

Embodiment 22k

A compound of Formula 1 or any one of Embodiments 1-22j wherein eachinstance of R¹⁴ is taken alone (i.e. not taken together with anotherinstance of R¹⁴ on an adjacent ring atom to form a ring).

Embodiment 22m

A compound of Formula 1 or any one of Embodiments 1-22d wherein R¹ isphenyl or a 6-membered heteroaromatic ring, each optionally substitutedwith up to 3 substituents independently selected from R¹⁴.

Embodiment 22 m1

A compound of Formula 1 or any one of Embodiments 1-22d wherein R¹ isphenyl or a 5- or 6-membered heteroaromatic ring, each optionallysubstituted with up to 3 substituents independently selected from R¹⁴.

Embodiment 22n

A compound of Embodiment 22m wherein R¹ is phenyl or pyridinyl, eachoptionally substituted with up to 3 substituents independently selectedfrom R¹⁴.

Embodiment 22o

A compound of Embodiments 22m or 22n wherein R¹⁴ is halogen, cyano,C(═NOR²¹)R²² or Z¹Q^(t); or C₁-C₈ alkyl, C₁-C₈ alkoxy or C₁-C₈alkylthio, each optionally substituted with halogen.

Embodiment 22o1

A compound of Embodiments 22m, 22 ml or 22n wherein R¹⁴ is halogen,cyano, C(═O)OR¹⁸, C(═O)NR²¹R¹⁹, C(═NOR²¹)R²² or Z¹Q^(t); or C₁-C₈ alkyl,C₁-C₈ alkoxy or C₁-C₈ alkylthio, each optionally substituted withhalogen.

Embodiment 22p

A compound of Embodiment 22o wherein R²¹ is C₁-C₄ alkyl.

Embodiment 22q

A compound of Embodiment 22o wherein R²² is C₁-C₄ alkyl.

Embodiment 22 r

A compound of Embodiment 22o wherein one R¹⁴ is Z¹Q^(t); Z¹ is a directbond; and Q^(t) is phenyl, pyridinyl or pyrimidinyl, each optionallysubstituted with up to 5 substituents independently selected from thegroup consisting of halogen, cyano, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₄alkoxy and C₁-C₄ haloalkoxy.

Embodiment 23

A compound of Formula 1 or any one of Embodiments 1-22r wherein R² is H,halogen, cyano, CHO, C(═O)R¹⁸, C(═O)OR¹⁸, C(═O)NR²¹R¹⁹, C(═S)NR²¹R¹⁹ orSO₂NR²¹R¹⁹; or C₁-C₈ alkyl, C₂-C₈ alkenyl, C₂-C₈ alkynyl, C₃-C₁₀cycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₆-C₁₄cycloalkylcycloalkyl, C₅-C₁₀ alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl,C₁-C₈ alkoxy, C₃-C₈ cycloalkoxy, C₄-C₁₀ cycloalkylalkoxy, C₂-C₈alkenyloxy, C₂-C₈ alkynyloxy, C₁-C₈ alkylthio, C₁-C₈ alkylsulfinyl,C₁-C₈ alkylsulfonyl, C₃-C₈ cycloalkylthio, C₃-C₈ cycloalkylsulfinyl,C₃-C₈ cycloalkylsulfonyl, C₄-C₁₀ cycloalkylalkylthio, C₄-C₁₀cycloalkylalkylsulfinyl, C₄-C₁₀ cycloalkylalkylsulfonyl, C₂-C₈alkenylthio, C₂-C₈ alkenylsulfinyl, C₂-C₈ alkenylsulfonyl, C₂-C₈alkynylthio, C₂-C₈ alkynylsulfinyl or C₂-C₈ alkynylsulfonyl, eachunsubstituted or substituted with at least one substituent independentlyselected from the group consisting of halogen, cyano, nitro, CHO,C(═O)OH, C(═O)NH₂, C(═O)R¹⁰, C(═O)OR¹¹, C(═O)NR¹²R¹³, OR¹¹, S(O)_(n)R¹⁰,SO₂NR¹²R¹³ and Si(R¹⁰)₃; or a 3- to 10-membered ring or a 7- to11-membered ring system, each ring or ring system containing ringmembers selected from carbon atoms and up to 4 heteroatoms independentlyselected from up to 2 O, up to 2 S, and up to 4 N, wherein up to 3carbon atom ring members are independently selected from C(═O) and C(═S)and the sulfur atom ring members are independently selected fromS(═O)_(u)(═NR²⁴)_(z), each ring or ring system optionally substitutedwith up to 5 substituents independently selected from R¹⁵.

Embodiment 23a

A compound of Embodiment 23 wherein R² is H, halogen, cyano, CHO,C(═O)R¹⁸ or C(═O)OR¹⁸; or C₁-C₈ alkyl, C₂-C₈ alkenyl, C₂-C₈ alkynyl,C₃-C₁₀ cycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl,C₆-C₁₄ cycloalkylcycloalkyl, C₅-C₁₀ alkylcycloalkylalkyl, C₃-C₈cycloalkenyl, C₁-C₈ alkoxy, C₃-C₈ cycloalkoxy, C₄-C₁₀ cycloalkylalkoxy,C₂-C₈ alkenyloxy or C₂-C₈ alkynyloxy, each unsubstituted or substitutedwith at least one substituent independently selected from the groupconsisting of halogen, cyano, nitro, CHO, C(═O)OH, C(═O)NH₂, C(═O)R¹⁰,C(═O)OR¹¹, C(═O)NR¹²R¹³, OR¹¹, S(O)_(n)R¹⁰, SO₂NR¹²R¹³ and Si(R¹⁰)₃; ora 3- to 10-membered ring or a 7- to 11-membered ring system, each ringor ring system containing ring members selected from carbon atoms and upto 4 heteroatoms independently selected from up to 2 O, up to 2 S, andup to 4 N, wherein up to 3 carbon atom ring members are independentlyselected from C(═O) and C(═S) and the sulfur atom ring members areindependently selected from S(═O)_(u)(═NR²⁴)_(z), each ring or ringsystem optionally substituted with up to 5 substituents independentlyselected from R¹⁵.

Embodiment 23b

A compound of Embodiment 23a wherein R² is H.

Embodiment 23c

A compound of Embodiment 23a wherein R² is halogen.

Embodiment 23d

A compound of Embodiment 23a wherein R² is cyano, CHO, C(═O)R¹⁸ orC(═O)OR¹⁸; or C₁-C₈ alkyl, C₂-C₈ alkenyl, C₂-C₈ alkynyl, C₃-C₁₀cycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₁-C₈alkoxy, C₃-C₈ cycloalkoxy or C₄-C₁₀ cycloalkylalkoxy, each unsubstitutedor substituted with at least one substituent independently selected fromthe group consisting of halogen, cyano, nitro, CHO, C(═O)OH, C(═O)NH₂,C(═O)R¹⁰, C(═O)OR¹¹, C(═O)NR¹²R¹³, OR¹¹, S(O)_(n)R¹⁰, SO₂NR¹²R¹³ andSi(R¹⁰)₃; or a 3- to 10-membered ring or a 7- to 11-membered ringsystem, each ring or ring system containing ring members selected fromcarbon atoms and up to 4 heteroatoms independently selected from up to 2O, up to 2 S, and up to 4 N, wherein up to 3 carbon atom ring membersare independently selected from C(═O) and C(═S) and the sulfur atom ringmembers are independently selected from S(═O)_(u)(═NR²⁴)_(z), each ringor ring system optionally substituted with up to 5 substituentsindependently selected from R¹⁵.

Embodiment 23e

A compound of Embodiment 23d wherein R² is C(═O)OR¹⁸; or C₁-C₈ alkyloptionally substituted with halogen; or a 3- to 10-membered ring or a 7-to to 11-membered ring system, each ring or ring system containing ringmembers selected from carbon atoms and up to 4 heteroatoms independentlyselected from up to 2 O, up to 2 S, and up to 4 N, wherein up to 3carbon atom ring members are independently selected from C(═O) and C(═S)and the sulfur atom ring members are independently selected fromS(═O)_(u)(═NR²⁴)_(z), each ring or ring system optionally substitutedwith up to 5 substituents independently selected from R¹⁵.

Embodiment 23f

A compound of Formula 1 or any one of Embodiments 1-23e whereininstances of R¹⁸ in the definition of R² are independently selected fromR^(18a); and R^(18a) is C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₈cycloalkyl, C₄-C₈ alkylcycloalkyl, C₄-C₈ cycloalkylalkyl, C₆-C₁₀cycloalkylcycloalkyl, C₅-C₁₀ alkylcycloalkylalkyl or C₃-C₆ cycloalkenyl,each unsubstituted or substituted with at least one substituentindependently selected from R^(17a);

-   -   R^(17a) is halogen, OR¹¹ or Z^(1c)Q^(t); and Z^(1c) is a direct        bond.

Embodiment 24

A compound of Embodiment 23e wherein R² is a 3- to 10-membered ring or a7- to 11-membered ring system, each ring or ring system containing ringmembers selected from carbon atoms and up to 4 heteroatoms independentlyselected from up to 2 O, up to 2 S, and up to 4 N, wherein up to 3carbon atom ring members are independently selected from C(═O) and C(═S)and the sulfur atom ring members are independently selected fromS(═O)_(u)(═NR²⁴)_(z), each ring or ring system optionally substitutedwith up to 5 substituents independently selected from R¹⁵.

Embodiment 24a

A compound of Embodiment 24 wherein R² is a 3- to 10-membered ringcontaining ring members selected from carbon atoms and up to 4heteroatoms independently selected from up to 2 O, up to 2 S, and up to4 N, wherein up to 3 carbon atom ring members are independently selectedfrom C(═O) and C(═S) and the sulfur atom ring members are independentlyselected from S(═O)_(u)(═NR²⁴)_(z), and optionally substituted with upto 5 substituents independently selected from R¹⁵.

Embodiment 24b

A compound of Embodiment 24a wherein the ring of R² is 5- or 6-membered.

Embodiment 24c

A compound of Embodiment 24b wherein the ring of R² is 5-membered andoptionally substituted with up to 3 substituents independently selectedfrom R¹⁵.

Embodiment 24d

A compound of Embodiment 24b wherein the ring of R² is 6-membered.

Embodiment 24e

A compound of Formula 1 or any one of Embodiments 1-24d wherein the ringor ring system of R² is partially unsaturated or aromatic (includingheteroaromatic).

Embodiment 24f

A compound of Embodiment 24e wherein the ring or ring system of R² isaromatic (including heteroaromatic).

Embodiment 24h

A compound of Formula 1 or any one of Embodiments 1-24f wherein the ringor ring system of R² is carbocyclic.

Embodiment 24i

A compound of Formula 1 or any one of Embodiments 1-24f wherein the ringor ring system of R² is heterocyclic.

Embodiment 25

A compound of Embodiment 24i wherein R² is pyridinyl, pyrimidinyl orthiazolyl, each optionally substituted with up to 3 substituentsindependently selected from the group consisting of halogen, cyano, SF₅,CHO, C(═O)R¹⁸, C(═O)OR¹⁸, C(═O)NR²¹R¹⁹ and Z¹Q^(t), and C₁-C₈ alkyl,C₂-C₈ alkenyl, C₂-C₈ alkynyl, C₃-C₁₀ cycloalkyl, C₄-C₁₀ alkylcycloalkyl,C₄-C₁₀ cycloalkylalkyl, C₁-C₈ alkoxy, C₃-C₈ cycloalkoxy, C₄-C₁₀cycloalkylalkoxy, C₂-C₈ alkenyloxy, C₂-C₈ alkynyloxy, C₁-C₈ alkylthio,C₁-C₈ alkylsulfinyl, C₁-C₈ alkylsulfonyl, C₃-C₈ cycloalkylthio, C₄-C₁₀cycloalkylalkylthio, C₂-C₈ alkenylthio and C₂-C₈ alkynylthio, eachunsubstituted or substituted with at least one substituent independentlyselected from the group consisting of halogen, OR¹¹ and Z¹Q^(t).

Embodiment 25a

A compound of Embodiment 24i wherein R² is pyridinyl, pyrimidinyl,oxazolyl or thiazolyl, each optionally substituted with up to 3substituents independently selected from the group consisting of halogenand C₁-C₄ alkyl.

Embodiment 25b

A compound of Embodiment 25 wherein R² is pyridinyl, pyrimidinyl orthiazolyl, each optionally substituted with up to 3 substituentsindependently selected from the group consisting of halogen and C₁-C₄alkyl.

Embodiment 25c

A compound of Embodiment 25b wherein R² is pyridinyl optionallysubstituted with at least one substituent independently selected fromthe group consisting of halogen and C₁-C₄ alkyl.

Embodiment 25d

A compound of Embodiment 25c wherein R² is pyridinyl optionallysubstituted with halogen.

Embodiment 25e

A compound of Embodiment 25d wherein R² is pyridinyl optionallysubstituted with Cl.

Embodiment 25f

A compound of Embodiment 25e wherein R² is 6-chloro-3-pyridinyl.

Embodiment 26

A compound of Embodiment 25b wherein R² is thiazolyl optionallysubstituted with at least one substituent independently selected fromthe group consisting of halogen or C₁-C₄ alkyl.

Embodiment 26a

A compound of Embodiment 26 wherein R² is thiazolyl optionallysubstituted with halogen.

Embodiment 26b

A compound of Embodiment 26a wherein R² is thiazolyl optionallysubstituted with Cl.

Embodiment 26c

A compound of Embodiment 26b wherein R² is 2-chloro-5-thiazolyl.

Embodiment 26d

A compound of Embodiment 25b wherein R² is pyrimidinyl optionallysubstituted with C₁-C₄ alkyl.

Embodiment 26e

A compound of Embodiment 24i wherein R² is N-methylpyrazolyl optionallysubstituted with C₁-C₄ alkyl.

Embodiment 26f

A compound of Embodiment 25b wherein R² is 6-chloro-3-pyridinyl or2-chloro-5-thiazolyl.

Embodiment 26g

A compound of Formula 1 or any one of Embodiments 1-26f wherein each R¹⁵is independently halogen, cyano, SF₅, CHO, C(═O)R¹⁸, C(═O)OR¹⁸,C(═O)NR²¹R¹⁹ or Z^(1c)Q^(t); or C₁-C₈ alkyl, C₂-C₈ alkenyl, C₂-C₈alkynyl, C₃-C₁₀ cycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀cycloalkylalkyl, C₁-C₈ alkoxy, C₃-C₈ cycloalkoxy, C₄-C₁₀cycloalkylalkoxy, C₂-C₈ alkenyloxy, C₂-C₈ alkynyloxy, C₁-C₈ alkylthio,C₁-C₈ alkylsulfinyl, C₁-C₈ alkylsulfonyl, C₃-C₈ cycloalkylthio, C₄-C₁₀cycloalkylalkylthio, C₂-C₈ alkenylthio, C₂-C₈ alkynylthio, eachunsubstituted or substituted with at least one substituent independentlyselected from R^(17a); R^(17a) is halogen, OR¹¹ or Z^(1d)Q^(t); Z^(1c)is a direct bond; and Z^(1d) is a direct bond.

Embodiment 27

A compound of Formula 1 or any one of Embodiments 1-26g wherein each R⁴and R⁵ is independently H, halogen, cyano, hydroxy, amino, nitro, OCN,SCN, CHO, C(═O)OH, C(═O)NH₂, C(═S)NH₂ or SO₂NH₂; or C₁-C₆ alkyl, C₂-C₆alkenyl, C₂-C₆ alkynyl, C₃-C₈ cycloalkyl, C₄-C₈ alkylcycloalkyl, C₄-C₈cycloalkylalkyl, C₆-C₁₂ cycloalkylcycloalkyl, C₅-C₈alkylcycloalkylalkyl, C₃-C₆ cycloalkenyl, C₁-C₆ alkoxy, C₃-C₆cycloalkoxy, C₄-C₈ cycloalkylalkoxy, C₂-C₆ alkenyloxy or C₂-C₆alkynyloxy, each unsubstituted or substituted with at least onesubstituent independently selected from the group consisting of halogen,cyano, nitro, CHO, C(═O)OH, C(═O)NH₂, C(═O)R¹⁰, C(═O)OR¹¹, C(═O)NR¹²R¹³,OR¹¹, S(O)_(n)R¹⁰, SO₂NR¹²R¹³ and Si(R¹⁰)₃.

Embodiment 27a

A compound of Embodiment 27 where each R⁴ and R⁵ is independently H orhalogen; or C₁-C₆ alkyl, C₃-C₈ cycloalkyl or C₁-C₆ alkoxy, eachoptionally substituted with halogen.

Embodiment 27b

A compound of Embodiment 27a where each R⁴ and R⁵ is independently H,halogen, C₁-C₂ alkyl or C₁-C₂ alkoxy.

Embodiment 27c

A compound of Embodiment 27b where each R⁴ and R⁵ is independently H,halogen or CH₃.

Embodiment 27d

A compound of Embodiment 27c wherein each R⁴ and R⁵ is independently Hor halogen.

Embodiment 27e

A compound of Formula 1 or any one of Embodiments 1-27d wherein each R⁵is H.

Embodiment 27f

A compound of Embodiment 27e wherein each R⁴ and R⁵ is H.

Embodiment 28

A compound of Formula 1 or any one of Embodiments 1-27f wherein each R⁶,R⁷ and R⁸ is independently H, C₁-C₆ alkyl, C₂-C₆ alkylcarbonyl or C₂-C₆alkoxycarbonyl.

Embodiment 29

A compound of Embodiment 28 wherein each R⁶, R⁷ and R⁸ is independentlyH, CH₃, C(═O)CH₃ or C(═O)OCH₃.

Embodiment 30

A compound of Formula 1 or any one of Embodiments 1-29 wherein each Z¹is a direct bond.

Embodiment 30a

A compound of Formula 1 or any one of Embodiments 1-29 wherein each Z¹is independently a direct bond or O.

Embodiment 31

A compound of Formula 1 or any one of Embodiments 1-30 wherein each R¹⁶is independently C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₈cycloalkyl, C₄-C₈ alkylcycloalkyl, C₄-C₈ cycloalkylalkyl, eachunsubstituted or substituted with at least one substituent independentlyselected from the group consisting of halogen, cyano, C₁-C₄ alkoxy,C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ haloalkylthio, C₂-C₄alkoxyalkyl, C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆alkylcarbonyloxy and C₃-C₈ dialkylaminocarbonyl.

Embodiment 32

A compound of Formula 1 or any one of Embodiments 1-31 wherein a is 1.

Embodiment 33

A compound of Formula 1 or any one of Embodiments 1-32 wherein each R²⁴is independently H, cyano, C₁-C₄ alkyl or C₁-C₄ alkoxy.

Embodiment 34

A compound of Formula 1 or any one of Embodiments 1-33 wherein in eachinstance of S(═O)_(u)(═NR²⁴)_(z), when z is 1 then u is 1.

Embodiment 35

A compound of Formula 1 or any one of Embodiments 1-34 wherein eachQ^(i) and Q^(t) is independently phenyl or pyridinyl, each optionallysubstituted with up to 5 substituents independently selected fromhalogen and C₁-C₄ haloalkyl.

Embodiment 35a

A compound of Formula 1 or any one of Embodiments 1-34 wherein eachQ^(t) is independently phenyl or a 5- or 6-membered heteroaromatic ring,each optionally substituted with up to 5 substituents independentlyselected from the group consisting of halogen, cyano, nitro, CHO,C(═O)OH, C(═O)NH₂, C(═O)R¹⁰, C(═O)OR¹¹, C(═O)NR¹²R¹³, C(═O)NR²¹NR²²R²³,OR¹¹, S(O)_(n)R¹⁰, SO₂NR¹²R¹³, S(═O)(═NR²¹)R²², Si(R¹⁰)₃ and R¹⁶.

Embodiment 36

A compound of Formula 1 or any one of Embodiments 1-34 wherein eachQ^(t) is independently phenyl, pyridinyl or pyrimidinyl, each optionallysubstituted with up to 5 substituents independently selected from thegroup consisting of halogen, cyano, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₄alkoxy and C₁-C₄ haloalkoxy.

Of note are compounds of Formula 1 or any one of Embodiments 1-36wherein X and Y are O, a composition comprising said compound, and itsuse for controlling an invertebrate pest.

Embodiments of this invention, including Embodiments 1-36 above as wellas any other embodiments described herein, can be combined in anymanner, and the descriptions of variables in the embodiments pertain notonly to the compounds of Formula 1 but also to the starting compoundsand intermediate compounds useful for preparing the compounds ofFormula 1. In addition, embodiments of this invention, includingEmbodiments 1-36 above as well as any other embodiments describedherein, and any combination thereof, pertain to the compositions andmethods of the present invention.

Combinations of Embodiments 1-36 are illustrated by:

Embodiment A

A compound of Formula 1 wherein

-   -   X is O;    -   Y is O;    -   Z is a direct bond, C(═X¹) or C(═X¹)E;    -   X¹ is O;    -   E is O;    -   A is C(R^(3c))═C(R^(3d)) or NR^(3e);    -   R¹ is C₁-C₈ alkyl optionally substituted with halogen; or a 3-        to 10-membered ring or a 7- to 11-membered ring system, each        ring or ring system containing ring members selected from carbon        atoms and up to 4 heteroatoms independently selected from up to        2 O, up to 2 S, and up to 4 N, wherein up to 3 carbon atom ring        members are independently selected from C(═O) and C(═S) and the        sulfur atom ring members are independently selected from        S(═O)_(u)(═NR²⁴)_(z), each ring or ring system optionally        substituted with up to 5 substituents independently selected        from R¹⁴;    -   R² is C(═O)OR¹⁸; or C₁-C₈ alkyl optionally substituted with        halogen; or a 3- to 10-membered ring or a 7- to 11-membered ring        system, each ring or ring system containing ring members        selected from carbon atoms and up to 4 heteroatoms independently        selected from up to 2 O, up to 2 S, and up to 4 N, wherein up to        3 carbon atom ring members are independently selected from C(═O)        and C(═S) and the sulfur atom ring members are independently        selected from S(═O)_(u)(═NR²⁴)_(z), each ring or ring system        optionally substituted with up to 5 substituents independently        selected from R¹⁵;    -   R^(3a), R^(3b), R^(3c) are independently H or halogen;    -   R^(3d) is halogen, C₁-C₈ alkyl, C₁-C₈ alkoxy, C₁-C₈ haloalkyl or        C₁-C₈ haloalkoxy; or R^(3c) and R^(3d) are taken together to        form a 5- to 7-membered carbocyclic or heterocyclic ring, each        ring containing ring members selected from carbon atoms and up        to 3 heteroatoms independently selected from up to 2 O, up to 2        S, and up to 3 N, wherein up to 2 carbon atom ring members are        independently selected from C(═O) and C(═S) and the sulfur atom        ring members are independently selected from S(═O)_(n), each        ring optionally substituted with up to 3 substituents        independently selected from the group consisting of halogen,        cyano, hydroxy, amino, nitro, C(═O)OH, C(═O)NH₂, SO₂NH₂, C₁-C₄        alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄        alkynyl, C₂-C₄ haloalkynyl, C₃-C₇ cycloalkyl, C₃-C₇        halocycloalkyl, C₄-C₈ alkylcycloalkyl, C₄-C₈        haloalkylcycloalkyl, C₄-C₈ cycloalkylalkyl, C₄-C₈        halocycloalkylalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₂-C₆        alkoxycarbonyl, C₂-C₆ haloalkoxycarbonyl, C₂-C₆ alkylcarbonyl        and C₂-C₆ haloalkylcarbonyl;    -   R^(3e) is C₁-C₄ alkyl;    -   R⁴ and R⁵ are H; and    -   a is 1.

Embodiment A1

A compound of Embodiment A wherein

-   -   R^(3d) is independently halogen, C₁-C₈ alkyl or C₁-C₈ alkoxy; or        R^(3c) and R^(3d) are taken together to form a 5- to 7-membered        carbocyclic or heterocyclic ring, each ring containing ring        members selected from carbon atoms and up to 3 heteroatoms        independently selected from up to 2 O, up to 2 S, and up to 3 N,        wherein up to 2 carbon atom ring members are independently        selected from C(═O) and C(═S) and the sulfur atom ring members        are independently selected from S(═O)_(n), each ring optionally        substituted with up to 3 substituents independently selected        from the group consisting of halogen, cyano, hydroxy, amino,        nitro, C(═O)OH, C(═O)NH₂, SO₂NH₂, C₁-C₄ alkyl, C₁-C₄ haloalkyl,        C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₂-C₄        haloalkynyl, C₃-C₇ cycloalkyl, C₃-C₇ halocycloalkyl, C₄-C₈        alkylcycloalkyl, C₄-C₈ haloalkylcycloalkyl, C₄-C₈        cycloalkylalkyl, C₄-C₈ halocycloalkylalkyl, C₁-C₆ alkoxy, C₁-C₆        haloalkoxy, C₂-C₆ alkoxycarbonyl, C₂-C₆ haloalkoxycarbonyl,        C₂-C₆ alkylcarbonyl and C₂-C₆ haloalkylcarbonyl.

Embodiment B

A compound of Embodiment A1 wherein

-   -   R¹ is phenyl or a 5- or 6-membered heteroaromatic ring, each        optionally substituted with up to 3 substituents independently        selected from R¹⁴;    -   R¹⁴ is halogen, cyano, C(═O)OR¹⁸, C(═O)NR²¹R¹⁹, C(═NOR²¹)R²² or        Z¹Q^(t); or C₁-C₈ alkyl, C₁-C₈ alkoxy or C₁-C₈ alkylthio, each        optionally substituted with halogen;    -   R²¹ is C₁-C₄ alkyl;    -   R²² is C₁-C₄ alkyl;    -   Z is a direct bond;    -   each Z¹ is independently a direct bond or O; and    -   each Q^(t) is independently phenyl or a 5- or 6-membered        heteroaromatic ring, each optionally substituted with up to 5        substituents independently selected from the group consisting of        halogen, cyano, nitro, CHO, C(═O)OH, C(═O)NH₂, C(═O)R¹⁰,        C(═O)OR¹¹, C(═O)NR¹²R¹³, C(═O)NR²¹NR²²R²³, OR¹¹, S(O)_(n)R¹⁰,        SO₂NR¹²R¹³, S(═O)(═NR²¹)R²², Si(R¹⁰)₃ and R¹⁶.

Embodiment B1

A compound of Embodiment B wherein

-   -   R¹ is phenyl optionally substituted with up to 3 substituents        independently selected from R¹⁴;    -   R¹⁴ is halogen, cyano, SF₅, CHO, C(═O)R¹⁸, C(═O)OR¹⁸,        C(═O)NR²¹R¹⁹, Z¹Q^(t) or Z¹Q^(i)Z¹Q^(t); or C₁-C₈ alkyl, C₂-C₈        alkenyl, C₂-C₈ alkynyl, C₃-C₁₀ cycloalkyl, C₄-C₁₀        alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₁-C₈ alkoxy, C₃-C₈        cycloalkoxy, C₄-C₁₀ cycloalkylalkoxy, C₂-C₈ alkenyloxy, C₂-C₈        alkynyloxy, C₁-C₈ alkylthio, C₁-C₈ alkylsulfinyl, C₁-C₈        alkylsulfonyl, C₃-C₈ cycloalkylthio, C₄-C₁₀ cycloalkylalkylthio,        C₂-C₈ alkenylthio or C₂-C₈ alkynylthio, each unsubstituted or        substituted with at least one substituent independently selected        from R^(17a);    -   R^(17a) is halogen, OR¹¹ or Z¹Q^(t);    -   R² is pyridinyl, pyrimidinyl or thiazolyl, each optionally        substituted with up to 3 substituents independently selected        from halogen, cyano, SF₅, CHO, C(═O)R¹⁸, C(═O)OR¹⁸,        C(═O)NR²¹R¹⁹, Z¹Q^(t); or C₁-C₈ alkyl, C₂-C₈ alkenyl, C₂-C₈        alkynyl, C₃-C₁₀ cycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀        cycloalkylalkyl, C₁-C₈ alkoxy, C₃-C₈ cycloalkoxy, C₄-C₁₀        cycloalkylalkoxy, C₂-C₈ alkenyloxy, C₂-C₈ alkynyloxy, C₁-C₈        alkylthio, C₁-C₈ alkylsulfinyl, C₁-C₈ alkylsulfonyl, C₃-C₈        cycloalkylthio, C₄-C₁₀ cycloalkylalkylthio, C₂-C₈ alkenylthio        and C₂-C₈ alkynylthio, each unsubstituted or substituted with at        least one substituent independently selected from the group        consisting of halogen, OR¹¹ and Z¹Q^(t);    -   each Z¹ is a direct bond; and    -   each Q^(i) and Q^(t) is independently phenyl or pyridinyl, each        optionally substituted with up to 5 substituents independently        selected from the group consisting of halogen and C₁-C₄        haloalkyl.

Embodiment C

A compound of Embodiment B1 wherein

-   -   A is C(R^(3c))═C(R^(3d));    -   Z is a direct bond;    -   R¹⁴ is halogen or Z¹Q^(t); or C₁-C₈ alkyl, C₁-C₈ alkoxy or C₁-C₈        alkylthio, each optionally substituted with halogen; and    -   R² is pyridinyl, pyrimidinyl or thiazolyl, each optionally        substituted with up to 3 substituents independently selected        from the group consisting of halogen and C₁-C₄ alkyl.

Embodiment D

A compound of Embodiment C wherein

-   -   R^(3a), R^(3b) and R^(3c) are H; and    -   R^(3d) is halogen, C₁-C₄ alkyl or C₁-C₄ alkoxy.

Embodiment E

A compound of Embodiment A wherein

-   -   R¹ is phenyl or a 6-membered heteroaromatic ring, each        optionally substituted with up to 3 substituents independently        selected from R¹⁴;    -   R¹⁴ is halogen, cyano, C(═NOR²¹)R²² or Z¹Q^(t); or C₁-C₈ alkyl,        C₁-C₈ alkoxy or C₁-C₈ alkylthio, each optionally substituted        with halogen;    -   R²¹ is C₁-C₄ alkyl;    -   R²² is C₁-C₄ alkyl;    -   Z is a direct bond; and    -   each Z¹ is a direct bond.

Embodiment F

A compound of Embodiment B wherein

-   -   R² is pyridinyl, pyrimidinyl, oxazolyl or thiazolyl, each        optionally substituted with up to 3 substituents independently        selected from the group consisting of halogen and C₁-C₄ alkyl.

Embodiment G

A compound of Embodiment F wherein

-   -   R¹ is phenyl or pyridinyl, each optionally substituted with up        to 3 substituents independently selected from R¹⁴; and    -   each Q^(t) is independently phenyl, pyridinyl or pyrimidinyl,        each optionally substituted with up to 5 substituents        independently selected from the group consisting of halogen,        cyano, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy and C₁-C₄        haloalkoxy.

Embodiment H

A compound of Embodiment G wherein

-   -   A is C(R^(3c))═C(R^(3d));    -   R^(3a), R^(3b) and R^(3c) are H; and    -   R^(3d) is halogen, C₁-C₄ alkyl or C₁-C₄ alkoxy.

Specific embodiments include compounds of Formula 1 selected from thegroup consisting of:

-   9-bromo-1-[(2-chloro-5-thiazolyl)methyl]-2-hydroxy-4-oxo-3-[3-(trifluoromethoxy)phenyl]-4H-pyrido[1,2-a]pyrimidinium    inner salt;-   9-bromo-1-[(2-chloro-5-thiazolyl)methyl]-2-hydroxy-4-oxo-3-[3-(trifluoromethyl)phenyl]-4H-pyrido[1,2-a]pyrimidinium    inner salt;-   9-bromo-3-(3-bromophenyl)-1-[(2-chloro-5-thiazolyl)methyl]-2-hydroxy-4-oxo-4H-pyrido[1,2-a]pyrimidinium    inner salt;-   9-bromo-1-[(2-chloro-5-thiazolyl)methyl]-3-[3-chloro-5-(trifluoromethyl)phenyl]-2-hydroxy-4-oxo-4H-pyrido[1,2-a]pyrimidinium    inner salt;-   9-bromo-3-[3-chloro-2-fluoro-5-(trifluoromethyl)phenyl]-1-[(2-chloro-5-thiazolyl)methyl]-2-hydroxy-4-oxo-4H-pyrido[1,2-a]pyrimidinium    inner salt;-   9-chloro-1-[(2-chloro-5-thiazolyl)methyl]-2-hydroxy-4-oxo-3-[3-(trifluoromethoxy)phenyl]-4H-pyrido[1,2-a]pyrimidinium    inner salt;-   1-[(2-chloro-5-thiazolyl)methyl]-2-hydroxy-9-methyl-4-oxo-3-[3-(trifluoromethoxy)phenyl]-4H-pyrido[1,2-a]pyrimidinium    inner salt;-   1-[(2-chloro-5-thiazolyl)methyl]-2-hydroxy-9-methyl-4-oxo-3-[3-(trifluoromethyl)phenyl]-4H-pyrido[1,2-a]pyrimidinium    inner salt;-   1-[(2-chloro-5-thiazolyl)methyl]-3-(2-fluorophenyl)-2-hydroxy-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidinium    inner salt;-   9-bromo-1-[(2-chloro-5-thiazolyl)methyl]-3-[3-chloro-5-(trifluoromethoxy)phenyl]-2-hydroxy-4-oxo-4H-pyrido[1,2-a]pyrimidinium    inner salt;-   1-[(2-chloro-5-thiazolyl)methyl]-3-[3-chloro-5-(trifluoromethoxy)phenyl]-2-hydroxy-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidinium    inner salt;-   1-[(2-chloro-5-thiazolyl)methyl]-3-(2,6-difluorophenyl)-2-hydroxy-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidinium    inner salt;-   1-[(2-chloro-5-thiazolyl)methyl]-2-hydroxy-9-methyl-4-oxo-3-[3-[(trifluoromethyl)thio]phenyl]-4H-pyrido[1,2-a]pyrimidinium    inner salt;-   3-(2-fluorophenyl)-2-hydroxy-9-methyl-4-oxo-1-(5-pyrimidinylmethyl)-4H-pyrido[1,2-a]pyrimidinium    inner salt;-   1-[(2-chloro-5-thiazolyl)methyl]-2-hydroxy-9-methyl-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidinium    inner salt;-   1-[(2-chloro-5-thiazolyl)methyl]-3-[2-fluoro-5-(trifluoromethyl)phenyl]-2-hydroxy-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidinium    inner salt;-   1-[(2-chloro-5-thiazolyl)methyl]-3-(4-fluorophenyl)-2-hydroxy-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidinium    inner salt;-   1-[(2-chloro-5-thiazolyl)methyl]-2-hydroxy-9-methoxy-4-oxo-3-[3-(trifluoromethoxy)phenyl]-4H-pyrido[1,2-a]pyrimidinium    inner salt;-   1-[(2-chloro-5-thiazolyl)methyl]-3-[2-fluoro-5-(trifluoromethyl)phenyl]-2-hydroxy-9-methoxy-4-oxo-4H-pyrido[1,2-a]pyrimidinium    inner salt;-   1-[(2-chloro-5-thiazolyl)methyl]-2-hydroxy-3-[2-methoxy-5-(trifluoromethoxy)phenyl]-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidinium    inner salt;-   1-[(2-chloro-5-thiazolyl)methyl]-2-hydroxy-3-(2-methoxyphenyl)-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidinium    inner salt;-   3-[3-chloro-2-fluoro-5-(trifluoromethyl)phenyl]-1-[(2-chloro-5-thiazolyl)methyl]-2-hydroxy-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidinium    inner salt;-   1-[(2-chloro-5-thiazolyl)methyl]-2-hydroxy-9-methyl-4-oxo-3-[4-[(trifluoromethyl)thio]phenyl]-4H-pyrido[1,2-a]pyrimidinium    inner salt;-   1-[(2-chloro-5-thiazolyl)methyl]-3-(2,4-difluorophenyl)-2-hydroxy-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidinium    inner salt;-   3-(3-chloro-2-fluorophenyl)-1-[(2-chloro-5-thiazolyl)methyl]-2-hydroxy-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidinium    inner salt;-   1-[(2-chloro-5-thiazolyl)methyl]-2-hydroxy-3-(3-methoxyphenyl)-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidinium    inner salt;-   7-bromo-1-[(2-chloro-5-thiazolyl)methyl]-3-[2-fluoro-3-(trifluoromethyl)phenyl]-2-hydroxy-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidinium    inner salt;-   1-[(2-chloro-5-thiazolyl)methyl]-2-hydroxy-3-(3-iodophenyl)-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidinium    inner salt;-   2-hydroxy-9-methyl-1-[(2-methyl-5-thiazolyl)methyl]-4-oxo-3-[3-(trifluoromethoxy)phenyl]-4H-pyrido[1,2-a]pyrimidinium    inner salt;-   2-hydroxy-9-methyl-1-[(2-methyl-5-thiazolyl)methyl]-4-oxo-3-[3-(trifluoromethyl)phenyl]-4H-pyrido[1,2-a]pyrimidinium    inner salt;-   3-(2-fluorophenyl)-2-hydroxy-9-methyl-1-[(2-methyl-5-thiazolyl)methyl]-4-oxo-4H-pyrido[1,2-a]pyrimidinium    inner salt;-   3-[3-bromo-5-(trifluoromethyl)phenyl]-1-[(2-chloro-5-thiazolyl)methyl]-2-hydroxy-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidinium    inner salt;-   3-[3-bromo-5-(trifluoromethoxy)phenyl]-1-[(2-chloro-5-thiazolyl)methyl]-2-hydroxy-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidinium    inner salt;-   1-[(2-chloro-5-thiazolyl)methyl]-3-[3-chloro-5-(trifluoromethyl)phenyl]-2-hydroxy-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidinium    inner salt;-   1-[(2-chloro-5-thiazolyl)methyl]-3-[3-fluoro-5-(trifluoromethyl)phenyl]-2-hydroxy-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidinium    inner salt;-   1-[(2-chloro-5-thiazolyl)methyl]-2-hydroxy-3-(3-iodo-5-methoxyphenyl)-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidinium    inner salt;-   3-(3-bromophenyl)-1-[(2-chloro-5-thiazolyl)methyl]-2-hydroxy-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidinium    inner salt;-   1-[(2-chloro-5-thiazolyl)methyl]-2-hydroxy-9-methyl-4-oxo-3-[3′-(trifluoromethoxy)[1,1′-biphenyl]-3-yl]-4H-pyrido[1,2-a]pyrimidinium    inner salt;-   1-[(2-chloro-5-thiazolyl)methyl]-3-(2′,5′-difluoro[1,1′-biphenyl]-3-yl)-2-hydroxy-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidinium    inner salt;-   3-[3-(6-chloro-3-pyridinyl)-5-(trifluoromethoxy)phenyl]-1-[(2-chloro-5-thiazolyl)methyl]-2-hydroxy-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidinium    inner salt;-   1-[(2-chloro-5-thiazolyl)methyl]-3-(2′,4′-dichloro[1,1′-biphenyl]-3-yl)-2-hydroxy-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidinium    inner salt;-   1-[(2-chloro-5-thiazolyl)methyl]-2-hydroxy-4-oxo-3-phenyl-4H-pyrimido[2,1-a]isoquinolinium    inner salt; and-   1-[(2-chloro-5-thiazolyl)methyl]-3-(3-ethenylphenyl)-2-hydroxy-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidinium    inner salt;

Further specific embodiments include compounds of Formula 1 selectedfrom the group consisting of compound numbers 113, 118, 125, 137, 183,190, 191, 196, 229, 231, 254, 257, 272, 289, 296, 299, 307, 308, 315,343, 344, 352, 363, 364, 368, 381, 385, 421, 433, 435, 448, 449, 450,451, 462, 482, 490 and 493, wherein the compound number refers tocompounds in Index Tables A-E.

An embodiment of this invention is directed to compounds of Formula 1(including all stereoisomers), N-oxides, and salts thereof, andcompositions containing them and their use for controlling invertebratepests:

wherein

-   -   X is O or S;    -   Y is O or S;    -   A is O, S, NR^(3e) or C(R^(3c))═C(R^(3d)), provided that the        C(R^(3c))═C(R^(3d)) moiety is oriented so the carbon atom bonded        to R^(3d) is connected directly to the pyrimidinium ring of        Formula 1;    -   Z is a direct bond, O, S(O)_(n), NR⁶, C(R⁷)₂O, OC(R⁷)₂, C(═X¹),        C(═X¹)E, EC(═X¹), C(═NOR⁸) or C(═NN(R⁶)₂);    -   X¹ is O, S or NR⁹;    -   E is O, S or NR^(9a);    -   R¹ is H, halogen, cyano, CHO, C(═O)OH, C(═O)NH₂ or C(═S)NH₂; or        C₁-C₈ alkyl, C₂-C₈ alkenyl, C₂-C₈ alkynyl, C₃-C₁₀ cycloalkyl,        C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₆-C₁₄        cycloalkylcycloalkyl, C₅-C₁₀ alkylcycloalkylalkyl or C₃-C₆        cycloalkenyl, each unsubstituted or substituted with at least        one substituent independently selected from the group consisting        of halogen, cyano, nitro, CHO, C(═O)OH, C(═O)NH₂, C(═O)R¹⁰,        C(═O)OR¹¹, C(═O)NR¹²R¹³, C(═O)NR²¹NR²²R²³, OR¹¹, S(O)_(n)R¹⁰,        SO₂NR¹²R¹³, S(═O)(═NR²¹)R²², Si(R¹⁰)₃ and Z¹Q^(t); or a 3- to        10-membered ring or a 7- to 11-membered ring system, each ring        or ring system containing ring members selected from carbon        atoms and up to 4 heteroatoms independently selected from up to        2 O, up to 2 S, and up to 4 N, wherein up to 3 carbon atom ring        members are independently selected from C(═O) and C(═S) and the        sulfur atom ring members are independently selected from        S(═O)_(u)(═NR²⁴)_(z), each ring or ring system optionally        substituted with up to 5 substituents independently selected        from R¹⁴; provided that when R¹ is halogen, then Z is a direct        bond, S(═O), S(═O)₂, OC(R⁷)₂, C(═X¹), EC(═X¹), C(═NOR⁸) or        C(═NN(R⁶)₂);    -   R² is H, halogen, cyano, hydroxy, amino, nitro, OCN, SCN, CHO,        C(═O)OH, C(═O)NH₂, C(═S)NH₂, SO₂NH₂, C(═O)R¹⁸, C(═O)OR¹⁸, NHR¹⁸,        NR¹⁸R¹⁹, C(═O)NR²¹R¹⁹, C(═S)NR²¹R¹⁹, SO₂NR²¹R¹⁹, OC(═O)R²¹,        OC(═O)OR¹⁸, OC(═O)NR²¹R¹⁹, N(R²¹)C(═O)R²¹, N(R²¹)C(═O)OR¹⁹,        N(R²¹)C(═O)NR²¹R²², OSO₂R¹⁸, OSO₂NR²¹R²², NR²¹SO₂R¹⁸,        NR²¹SO₂NR²¹R²² or Si(R¹⁸R¹⁹R²⁰); or C₁-C₈ alkyl, C₂-C₈ alkenyl,        C₂-C₈ alkynyl, C₃-C₁₀ cycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀        cycloalkylalkyl, C₆-C₁₄ cycloalkylcycloalkyl, C₅-C₁₀        alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl, C₁-C₈ alkoxy, C₃-C₈        cycloalkoxy, C₄-C₁₀ cycloalkylalkoxy, C₂-C₈ alkenyloxy, C₂-C₈        alkynyloxy, C₁-C₈ alkylthio, C₁-C₈ alkylsulfinyl, C₁-C₈        alkylsulfonyl, C₃-C₈ cycloalkylthio, C₃-C₈ cycloalkylsulfinyl,        C₃-C₈ cycloalkylsulfonyl, C₄-C₁₀ cycloalkylalkylthio, C₄-C₁₀        cycloalkylalkylsulfinyl, C₄-C₁₀ cycloalkylalkylsulfonyl, C₂-C₈        alkenylthio, C₂-C₈ alkenylsulfinyl, C₂-C₈ alkenylsulfonyl, C₂-C₈        alkynylthio, C₂-C₈ alkynylsulfinyl or C₂-C₈ alkynylsulfonyl,        each unsubstituted or substituted with at least one substituent        independently selected from the group consisting of halogen,        cyano, nitro, CHO, C(═O)OH, C(═O)NH₂, C(═O)R¹⁰, C(═O)OR¹¹,        C(═O)NR¹²R¹³, OR¹¹, S(O)_(n)R¹⁰, SO₂NR¹²R¹³ and Si(R¹⁰)₃; or a        3- to 10-membered ring or a 7- to 11-membered ring system, each        ring or ring system containing ring members selected from carbon        atoms and up to 4 heteroatoms independently selected from up to        2 O, up to 2 S, and up to 4 N, wherein up to 3 carbon atom ring        members are independently selected from C(═O) and C(═S) and the        sulfur atom ring members are independently selected from        S(═O)_(u)(═NR²⁴)_(z), each ring or ring system optionally        substituted with up to 5 substituents independently selected        from R¹⁵;    -   R^(3a), R^(3b), R^(3c) and R^(3d) are independently H, halogen,        cyano, hydroxy, amino, nitro, SF₅, OCN, SCN, CHO, C(═O)OH,        C(═O)NH₂, C(═S)NH₂, SO₂NH₂, C(═O)R¹⁸, C(═O)OR¹⁸, NHR¹⁸, NR¹⁸R¹⁹,        C(═O)NR²¹R¹⁹, C(═S)NR²¹R¹⁹, SO₂NR²¹R¹⁹, OC(═O)R²¹, OC(═O)OR¹⁸,        OC(═O)NR²¹R¹⁹, N(R²¹)C(═O)R²¹, N(R²¹)C(═O)OR¹⁹,        N(R²¹)C(═O)NR²¹R²², OSO₂R¹⁸, OSO₂NR²¹R²², NR²¹SO₂R¹⁸,        NR²¹SO₂NR²¹R²², Si(R¹⁸R¹⁹R²⁰) or Z¹Q^(t); or C₁-C₈ alkyl, C₂-C₈        alkenyl, C₂-C₈ alkynyl, C₃-C₁₀ cycloalkyl, C₄-C₁₀        alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₆-C₁₄        cycloalkylcycloalkyl, C₅-C₁₀ alkylcycloalkylalkyl, C₃-C₈        cycloalkenyl, C₁-C₈ alkoxy, C₃-C₈ cycloalkoxy, C₄-C₁₀        cycloalkylalkoxy, C₂-C₈ alkenyloxy, C₂-C₈ alkynyloxy, C₁-C₈        alkylthio, C₁-C₈ alkylsulfinyl, C₁-C₈ alkylsulfonyl, C₃-C₈        cycloalkylthio, C₃-C₈ cycloalkylsulfinyl, C₃-C₈        cycloalkylsulfonyl, C₄-C₁₀ cycloalkylalkylthio, C₄-C₁₀        cycloalkylalkylsulfinyl, C₄-C₁₀ cycloalkylalkylsulfonyl, C₂-C₈        alkenylthio, C₂-C₈ alkenylsulfinyl, C₂-C₈ alkenylsulfonyl, C₂-C₈        alkynylthio, C₂-C₈ alkynylsulfinyl or C₂-C₈ alkynylsulfonyl,        each unsubstituted or substituted with at least one substituent        independently selected from R¹⁷; or R^(3a) and R^(3b), or R^(3b)        and R^(3c), or R^(3c) and R^(3d) are taken together with the        adjacent carbon atoms to which they are attached to form a 5- to        7-membered carbocyclic or heterocyclic ring, each ring        containing ring members selected from carbon atoms and up to 3        heteroatoms independently selected from up to 2 O, up to 2 S,        and up to 3 N, wherein up to 2 carbon atom ring members are        independently selected from C(═O) and C(═S) and the sulfur atom        ring members are independently selected from S(═O)_(n), each        ring optionally substituted with up to 3 substituents        independently selected from the group consisting of halogen,        cyano, hydroxy, amino, nitro, C(═O)OH, C(═O)NH₂, SO₂NH₂, C₁-C₄        alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄        alkynyl, C₂-C₄ haloalkynyl, C₃-C₇ cycloalkyl, C₃-C₇        halocycloalkyl, C₄-C₈ alkylcycloalkyl, C₄-C₈        haloalkylcycloalkyl, C₄-C₈ cycloalkylalkyl, C₄-C₈        halocycloalkylalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₂-C₆        alkoxycarbonyl, C₂-C₆ haloalkoxycarbonyl, C₂-C₆ alkylcarbonyl        and C₂-C₆ haloalkylcarbonyl;    -   R^(3e) is H, hydroxy, amino, CHO, C(═O)NH₂, C(═S)NH₂, SO₂NH₂,        C(═O)R¹⁸, C(═O)OR¹⁸, NHR¹⁸, NR¹⁸R¹⁹, C(═O)NR²¹R¹⁹, C(═S)NR²¹R¹⁹,        SO₂NR²¹R¹⁹, OC(═O)R²¹, OC(═O)OR¹⁸, OC(═O)NR²¹R¹⁹,        N(R²¹)C(═O)R²¹, N(R²¹)C(═O)OR¹⁹, N(R²¹)C(═O)NR²¹R²², OSO₂R¹⁸,        OSO₂NR²¹R²², NR²¹SO₂R¹⁸, NR²¹SO₂NR²¹R²², Si(R¹⁸R¹⁹R²⁰) or        Z¹Q^(t); or C₁-C₈ alkyl, C₂-C₈ alkenyl, C₂-C₈ alkynyl, C₃-C₁₀        cycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl,        C₆-C₁₄ cycloalkylcycloalkyl, C₅-C₁₀ alkylcycloalkylalkyl, C₃-C₈        cycloalkenyl, C₁-C₈ alkoxy, C₃-C₈ cycloalkoxy, C₄-C₁₀        cycloalkylalkoxy, C₂-C₈ alkenyloxy, C₂-C₈ alkynyloxy, C₁-C₈        alkylsulfinyl, C₁-C₈ alkylsulfonyl, C₃-C₈ cycloalkylsulfinyl,        C₃-C₈ cycloalkylsulfonyl, C₄-C₁₀ cycloalkylalkylsulfinyl, C₄-C₁₀        cycloalkylalkylsulfonyl, C₂-C₈ alkenylsulfinyl, C₂-C₈        alkenylsulfonyl, C₂-C₈ alkynylsulfinyl or C₂-C₈ alkynylsulfonyl,        each unsubstituted or substituted with at least one substituent        independently selected from R¹⁷; or R^(3e) and R^(3b) are taken        together with the adjacent carbon atoms to which they are        attached to form a 5- to 7-membered carbocyclic or heterocyclic        ring, each ring containing ring members selected from carbon        atoms and up to 3 heteroatoms independently selected from up to        2 O, up to 2 S, and up to 3 N, wherein up to 2 carbon atom ring        members are independently selected from C(═O) and C(═S) and the        sulfur atom ring members are independently selected from        S(═O)_(n), each ring optionally substituted with up to 3        substituents independently selected from the group consisting of        halogen, cyano, hydroxy, amino, nitro, C(═O)OH, C(═O)NH₂,        SO₂NH₂, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄        haloalkenyl, C₂-C₄ alkynyl, C₂-C₄ haloalkynyl, C₃-C₇ cycloalkyl,        C₃-C₇ halocycloalkyl, C₄-C₈ alkylcycloalkyl, C₄-C₈        haloalkylcycloalkyl, C₄-C₈ cycloalkylalkyl, C₄-C₈        halocycloalkylalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₂-C₆        alkoxycarbonyl, C₂-C₆ haloalkoxycarbonyl, C₂-C₆ alkylcarbonyl        and C₂-C₆ haloalkylcarbonyl;    -   each R⁴ and R⁵ is independently H, halogen, cyano, hydroxy,        amino, nitro, OCN, SCN, CHO, C(═O)OH, C(═O)NH₂, C(═S)NH₂ or        SO₂NH₂; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₈        cycloalkyl, C₄-C₈ alkylcycloalkyl, C₄-C₈ cycloalkylalkyl, C₆-C₁₂        cycloalkylcycloalkyl, C₅-C₈ alkylcycloalkylalkyl, C₃-C₆        cycloalkenyl, C₁-C₆ alkoxy, C₃-C₆ cycloalkoxy, C₄-C₈        cycloalkylalkoxy, C₂-C₆ alkenyloxy or C₂-C₆ alkynyloxy, each        unsubstituted or substituted with at least one substituent        independently selected from the group consisting of halogen,        cyano, nitro, CHO, C(═O)OH, C(═O)NH₂, C(═O)R¹⁰, C(═O)OR¹¹,        C(═O)NR¹²R¹³, OR¹¹, S(O)_(n)R¹⁰, SO₂NR¹²R¹³ and Si(R¹⁰)₃;    -   each R⁶, R⁷ and R⁸ is independently H; or C₁-C₆ alkyl, C₂-C₆        alkenyl, C₂-C₆ alkynyl, C₃-C₈ cycloalkyl, C₄-C₈ alkylcycloalkyl,        C₄-C₈ cycloalkylalkyl, C₆-C₁₀ cycloalkylcycloalkyl, C₅-C₁₀        alkylcycloalkylalkyl, C₃-C₆ cycloalkenyl, C₂-C₆ alkylcarbonyl or        C₂-C₆ alkoxycarbonyl, each unsubstituted or substituted with at        least one substituent independently selected from the group        consisting of halogen, cyano, nitro, CHO, C(═O)OH, C(═O)NH₂,        C(═O)R¹⁰, C(═O)OR¹¹, C(═O)NR¹²R¹³, OR¹¹, S(O)_(n)R¹⁰, SO₂NR¹²R¹³        and Si(R¹⁰)₃;    -   each R⁹ is independently C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆        alkynyl, C₃-C₈ cycloalkyl, C₄-C₈ alkylcycloalkyl, C₄-C₈        cycloalkylalkyl, C₆-C₁₀ cycloalkylcycloalkyl, C₅-C₁₀        alkylcycloalkylalkyl, C₃-C₆ cycloalkenyl, C₂-C₆ alkylcarbonyl or        C₂-C₆ alkoxycarbonyl, each unsubstituted or substituted with at        least one substituent independently selected from the group        consisting of halogen, cyano, nitro, CHO, C(═O)OH, C(═O)NH₂,        C(═O)R¹⁰, C(═O)OR¹¹, C(═O)NR¹²R¹³, OR¹¹, S(O)_(n)R¹⁰, SO₂NR¹²R¹³        and Si(R¹⁰)₃;    -   each R^(9a) is independently H; or C₁-C₆ alkyl, C₂-C₆ alkenyl,        C₂-C₆ alkynyl, C₃-C₈ cycloalkyl, C₄-C₈ alkylcycloalkyl, C₄-C₈        cycloalkylalkyl, C₆-C₁₀ cycloalkylcycloalkyl, C₅-C₁₀        alkylcycloalkylalkyl, C₃-C₆ cycloalkenyl, C₂-C₆ alkylcarbonyl or        C₂-C₆ alkoxycarbonyl, each unsubstituted or substituted with at        least one substituent independently selected from the group        consisting of halogen, cyano, nitro, CHO, C(═O)OH, C(═O)NH₂,        C(═O)R¹⁰, C(═O)OR¹¹, C(═O)NR¹²R¹³, OR¹¹, S(O)_(n)R¹⁰, SO₂NR¹²R¹³        and Si(R¹⁰)₃;    -   each R¹⁰, R¹¹, R¹² and R¹³ is independently C₁-C₆ alkyl, C₂-C₆        alkenyl, C₂-C₆ alkynyl, C₃-C₈ cycloalkyl, C₄-C₈ alkylcycloalkyl,        C₄-C₈ cycloalkylalkyl, C₆-C₁₀ cycloalkylcycloalkyl, C₅-C₁₀        alkylcycloalkylalkyl or C₃-C₆ cycloalkenyl, each unsubstituted        or substituted with at least one substituent independently        selected from the group consisting of halogen, cyano, nitro,        CHO, C(═O)OH, C(═O)NH₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄        alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄        haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl,        C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino,        C₂-C₄ alkoxyalkyl, C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl,        C₂-C₆ alkylcarbonyloxy, C₂-C₆ alkylcarbonylthio, C₂-C₆        alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl and C₃-C₆        trialkylsilyl; or phenyl or a 5- or 6-membered heteroaromatic        ring, each unsubstituted or substituted with at least one        substituent independently selected from the group consisting of        C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl,        C₃-C₈ cycloalkyl, C₄-C₈ alkylcycloalkyl, C₄-C₈ cycloalkylalkyl,        C₆-C₁₀ cycloalkylcycloalkyl, C₅-C₁₀ alkylcycloalkylalkyl, C₃-C₆        cycloalkenyl, halogen, cyano, nitro, CHO, C(═O)OH, C(═O)NH₂,        C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄        alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄        haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl, C₁-C₄ alkylamino,        C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₂-C₄ alkoxyalkyl,        C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆        alkylcarbonyloxy, C₂-C₆ alkylcarbonylthio, C₂-C₆        alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl and C₃-C₆        trialkylsilyl;    -   each R¹⁴ is independently halogen, cyano, hydroxy, amino, nitro,        SF₅, OCN, SCN, CHO, C(═O)OH, C(═O)NH₂, C(═S)NH₂, SO₂NH₂,        C(═O)R¹⁸, C(═O)OR¹⁸, NHR¹⁸, NR¹⁸R¹⁹, C(═O)NR²¹R¹⁹,        C(═O)NR²¹NR²²R²³, C(═S)NR²¹R¹⁹, SO₂NR²¹R¹⁹, OC(═O)R²¹,        OC(═O)OR¹⁸, OC(═O)NR²¹R¹⁹, N(R²¹)C(═O)R²¹, N(R²¹)C(═O)OR¹⁹,        N(R²¹)C(═O)NR²¹R²², OSO₂R¹⁸, OSO₂NR²¹R²², NR²¹SO₂R¹⁸,        NR²¹SO₂NR²¹R²², Si(R¹⁸R¹⁹R²⁰), C(═NR²¹)R²², C(═NOR²¹)R²²,        C(═NNR²¹R²²)R²³, C(═NN(C(═O)R¹⁹)R²¹)R²²,        C(═NN(C(═O)OR¹⁹)R²¹)R²², ON═CR²¹R²², ONR²¹R²², S(═O)(═NR²¹)R²²,        SO₂NR²¹C(═O)NR²²R²³, P(═X²)R¹⁸R¹⁹, OP(═X²)R¹⁸R¹⁹,        OP(═X²)(OR¹⁸)R¹⁹, OP(═X²)(OR¹⁸)OR¹⁹, N═CR²¹R²²,        NR²¹N═CR²²R²³NR²¹NR²²R²³, NR²¹C(═X²)NR²²R²³,        NR²¹C(═NR²¹)NR²²R²³, NR²¹NR²¹C(═X²)NR²²R²³, NR²¹NR²¹SO₂NR²²R²³,        Z¹Q^(t) or Z¹Q^(i)Z¹Q^(t); or C₁-C₈ alkyl, C₂-C₈ alkenyl, C₂-C₈        alkynyl, C₃-C₁₀ cycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀        cycloalkylalkyl, C₆-C₁₄ cycloalkylcycloalkyl, C₅-C₁₀        alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl, C₁-C₈ alkoxy, C₃-C₈        cycloalkoxy, C₄-C₁₀ cycloalkylalkoxy, C₂-C₈ alkenyloxy, C₂-C₈        alkynyloxy, C₁-C₈ alkylthio, C₁-C₈ alkylsulfinyl, C₁-C₈        alkylsulfonyl, C₃-C₈ cycloalkylthio, C₃-C₈ cycloalkylsulfinyl,        C₃-C₈ cycloalkylsulfonyl, C₄-C₁₀ cycloalkylalkylthio, C₄-C₁₀        cycloalkylalkylsulfinyl, C₄-C₁₀ cycloalkylalkylsulfonyl, C₂-C₈        alkenylthio, C₂-C₈ alkenylsulfinyl, C₂-C₈ alkenylsulfonyl, C₂-C₈        alkynylthio, C₂-C₈ alkynylsulfinyl or C₂-C₈ alkynylsulfonyl,        each unsubstituted or substituted with at least one substituent        independently selected from R¹⁷; or    -   two R¹⁴ substituents on adjacent ring atoms are taken together        with the adjacent ring atoms to form a 5- to 7-membered        carbocyclic or heterocyclic ring, each ring containing ring        members selected from carbon atoms and up to 3 heteroatoms        independently selected from up to 2 O, up to 2 S, and up to 3 N,        wherein up to 2 carbon atom ring members are independently        selected from C(═O) and C(═S) and the sulfur atom ring members        are independently selected from S(═O)_(n), each ring optionally        substituted with up to 3 substituents independently selected        from the group consisting of halogen, cyano, hydroxy, amino,        nitro, C(═O)OH, C(═O)NH₂, SO₂NH₂, C₁-C₄ alkyl, C₁-C₄ haloalkyl,        C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₂-C₄        haloalkynyl, C₃-C₇ cycloalkyl, C₃-C₇ halocycloalkyl, C₄-C₈        alkylcycloalkyl, C₄-C₈ haloalkylcycloalkyl, C₄-C₈        cycloalkylalkyl, C₄-C₈ halocycloalkylalkyl, C₁-C₆ alkoxy, C₁-C₆        haloalkoxy, C₂-C₆ alkoxycarbonyl, C₂-C₆ haloalkoxycarbonyl,        C₂-C₆ alkylcarbonyl and C₂-C₆ haloalkylcarbonyl;    -   each X² is independently O or S;    -   each Z¹ is independently a direct bond, O, S(O)_(n), NR⁶,        C(R⁷)₂, C(R⁷)═C(R⁷), C≡C, C(R⁷)₂O, OC(R⁷)₂, C(═X¹), C(═X¹)E,        EC(═X¹), C(═NOR⁸) or C(═NN(R⁶)₂);    -   each Q^(i) is independently a 3- to 10-membered ring or a 7- to        11-membered ring system, each ring or ring system containing        ring members selected from carbon atoms and up to 4 heteroatoms        independently selected from up to 2 O, up to 2 S, and up to 4 N,        wherein up to 3 carbon atom ring members are independently        selected from C(═O) and C(═S) and the sulfur atom ring members        are independently selected from S(═O)_(u)(═NR²⁴)_(z), each ring        or ring system optionally substituted with up to 4 substituents        independently selected from the group consisting of halogen,        cyano, nitro, CHO, C(═O)OH, C(═O)NH₂, C(═O)R¹⁰, C(═O)OR¹¹,        C(═O)NR¹²R¹³, OR¹¹, S(O)_(n)R¹⁰, SO₂NR¹²R¹³, Si(R¹⁰)₃ and R¹⁶;    -   each Q^(t) is independently a 3- to 10-membered ring or a 7- to        11-membered ring system, each ring or ring system containing        ring members selected from carbon atoms and up to 4 heteroatoms        independently selected from up to 2 O, up to 2 S, and up to 4 N,        wherein up to 3 carbon atom ring members are independently        selected from C(═O) and C(═S) and the sulfur atom ring members        are independently selected from S(═O)_(u)(═NR²⁴)_(z), each ring        or ring system optionally substituted with up to 5 substituents        independently selected from the group consisting of halogen,        cyano, nitro, CHO, C(═O)OH, C(═O)NH₂, C(═O)R¹⁰, C(═O)OR¹¹,        C(═O)NR¹²R¹³, C(═O)NR²¹NR²²R²³, OR¹¹, S(O)_(n)R¹⁰, SO₂NR¹²R¹³,        S(═O)(═NR²¹)R²², Si(R¹⁰)₃ and R¹⁶;    -   each R¹⁵ is independently halogen, cyano, hydroxy, amino, nitro,        SF₅, OCN, SCN, CHO, C(═O)OH, C(═O)NH₂, C(═S)NH₂, SO₂NH₂,        C(═O)R¹⁸, C(═O)OR¹⁸, NHR¹⁸, NR¹⁸R¹⁹, C(═O)NR²¹R¹⁹,        C(═O)NR²¹NR²²R²³, C(═S)NR²¹R¹⁹, SO₂NR²¹R¹⁹, S(═O)(═NR²¹)R²²,        OC(═O)R²¹, OC(═O)OR¹⁸, OC(═O)NR²¹R¹⁹N(R²¹)C(═O)R²¹,        N(R²¹)C(═O)OR¹⁹, N(R²¹)C(═O)NR²¹R²², OSO₂R¹⁸, OSO₂NR²¹R²²,        NR²¹SO₂R¹⁸, NR²¹SO₂NR²¹R²², Si(R¹⁸R¹⁹R²⁰) or Z¹Q^(t); or C₁-C₈        alkyl, C₂-C₈ alkenyl, C₂-C₈ alkynyl, C₃-C₁₀ cycloalkyl, C₄-C₁₀        alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₆-C₁₄        cycloalkylcycloalkyl, C₅-C₁₀ alkylcycloalkylalkyl, C₃-C₈        cycloalkenyl, C₁-C₈ alkoxy, C₃-C₈ cycloalkoxy, C₄-C₁₀        cycloalkylalkoxy, C₂-C₈ alkenyloxy, C₂-C₈ alkynyloxy, C₁-C₈        alkylthio, C₁-C₈ alkylsulfinyl, C₁-C₈ alkylsulfonyl, C₃-C₈        cycloalkylthio, C₃-C₈ cycloalkylsulfinyl, C₃-C₈        cycloalkylsulfonyl, C₄-C₁₀ cycloalkylalkylthio, C₄-C₁₀        cycloalkylalkylsulfinyl, C₄-C₁₀ cycloalkylalkylsulfonyl, C₂-C₈        alkenylthio, C₂-C₈ alkenylsulfinyl, C₂-C₈ alkenylsulfonyl, C₂-C₈        alkynylthio, C₂-C₈ alkynylsulfinyl or C₂-C₈ alkynylsulfonyl,        each unsubstituted or substituted with at least one substituent        independently selected from R¹⁷; or    -   two R¹⁵ substituents on adjacent ring atoms are taken together        with the adjacent ring atoms to form a 5- to 7-membered        carbocyclic or heterocyclic ring, each ring containing ring        members selected from carbon atoms and up to 3 heteroatoms        independently selected from up to 2 O, up to 2 S, and up to 3 N,        wherein up to 2 carbon atom ring members are independently        selected from C(═O) and C(═S) and the sulfur atom ring members        are independently selected from S(═O)_(n), each ring optionally        substituted with up to 3 substituents independently selected        from the group consisting of halogen, cyano, hydroxy, amino,        nitro, C(═O)OH, C(═O)NH₂, SO₂NH₂, C₁-C₄ alkyl, C₁-C₄ haloalkyl,        C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₂-C₄        haloalkynyl, C₃-C₇ cycloalkyl, C₃-C₇ halocycloalkyl, C₄-C₈        alkylcycloalkyl, C₄-C₈ haloalkylcycloalkyl, C₄-C₈        cycloalkylalkyl, C₄-C₈ halocycloalkylalkyl, C₁-C₆ alkoxy, C₁-C₆        haloalkoxy, C₂-C₆ alkoxycarbonyl, C₂-C₆ haloalkoxycarbonyl,        C₂-C₆ alkylcarbonyl and C₂-C₆ haloalkylcarbonyl;    -   each R¹⁶ is independently C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆        alkynyl, C₃-C₈ cycloalkyl, C₄-C₈ alkylcycloalkyl, C₄-C₈        cycloalkylalkyl, C₆-C₁₀ cycloalkylcycloalkyl, C₅-C₁₀        alkylcycloalkylalkyl or C₃-C₆ cycloalkenyl, each unsubstituted        or substituted with at least one substituent independently        selected from the group consisting of halogen, cyano, nitro,        CHO, C(═O)OH, C(═O)NH₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄        alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄        haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl,        C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino,        C₂-C₄ alkoxyalkyl, C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl,        C₂-C₆ alkylcarbonyloxy, C₂-C₆ alkylcarbonylthio, C₂-C₆        alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl and C₃-C₆        trialkylsilyl; or phenyl or a 5- or 6-membered heteroaromatic        ring, each unsubstituted or substituted with at least one        substituent independently selected from the group consisting of        C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₈ cycloalkyl,        C₄-C₈ alkylcycloalkyl, C₄-C₈ cycloalkylalkyl, C₆-C₁₀        cycloalkylcycloalkyl, C₅-C₁₀ alkylcycloalkylalkyl, C₃-C₆        cycloalkenyl, halogen, cyano, nitro, CHO, C(═O)OH, C(═O)NH₂,        C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄        alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄        haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl, C₁-C₄ alkylamino,        C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₂-C₄ alkoxyalkyl,        C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆        alkylcarbonyloxy, C₂-C₆ alkylcarbonylthio, C₂-C₆        alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl and C₃-C₆        trialkylsilyl;    -   each R¹⁷ is independently halogen, cyano, nitro, OH, CHO,        C(═O)OH, C(═O)NH₂, C(═O)R¹⁰, C(═O)OR¹¹, C(═O)NR¹²R¹³, OR¹¹,        S(O)_(n)R¹⁰, SO₂NR¹²R¹³, Si(R¹⁰)₃ or Z¹Q^(t);    -   each R¹⁸, R¹⁹ and R²⁰ is independently Q^(t); or C₁-C₆ alkyl,        C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₈ cycloalkyl, C₄-C₈        alkylcycloalkyl, C₄-C₈ cycloalkylalkyl, C₆-C₁₀        cycloalkylcycloalkyl, C₅-C₁₀ alkylcycloalkylalkyl or C₃-C₆        cycloalkenyl, each unsubstituted or substituted with at least        one substituent independently selected from R¹⁷;    -   each R²¹, R²² and R²³ is independently Q^(t) or H; or C₁-C₆        alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₈ cycloalkyl, C₄-C₈        alkylcycloalkyl, C₄-C₈ cycloalkylalkyl, C₆-C₁₀        cycloalkylcycloalkyl, C₅-C₁₀ alkylcycloalkylalkyl or C₃-C₆        cycloalkenyl, each unsubstituted or substituted with at least        one substituent independently selected from R¹⁷;    -   each R²⁴ is independently H, cyano, OCN, SCN, CHO, C(═O)OH,        C(═O)NH₂, C(═S)NH₂, SO₂NH₂, C(═O)R¹⁸, C(═O)OR¹⁸, NHR¹⁸, NR¹⁸R¹⁹,        C(═O)NR²¹R¹⁹, C(═S)NR²¹R¹⁹, SO₂NR²¹R¹⁹, OC(═O)R²¹, OC(═O)OR¹⁸,        OC(═O)NR²¹R¹⁹, N(R²¹)C(═O)R²¹, N(R²¹)C(═O)OR¹⁹,        N(R²¹)C(═O)NR²¹R²², OSO₂R¹⁸, OSO₂NR²¹R²², NR²¹SO₂R¹⁸,        NR²¹SO₂NR²¹R²², Si(R¹⁸R¹⁹R²⁰) or Z¹Q^(t); or C₁-C₈ alkyl, C₂-C₈        alkenyl, C₂-C₈ alkynyl, C₃-C₁₀ cycloalkyl, C₄-C₁₀        alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₆-C₁₄        cycloalkylcycloalkyl, C₅-C₁₀ alkylcycloalkylalkyl, C₃-C₈        cycloalkenyl, C₁-C₈ alkoxy, C₃-C₈ cycloalkoxy, C₄-C₁₀        cycloalkylalkoxy, C₂-C₈ alkenyloxy, C₂-C₈ alkynyloxy, C₁-C₈        alkylthio, C₁-C₈ alkylsulfinyl, C₁-C₈ alkylsulfonyl, C₃-C₈        cycloalkylthio, C₃-C₈ cycloalkylsulfinyl, C₃-C₈        cycloalkylsulfonyl, C₄-C₁₀ cycloalkylalkylthio, C₄-C₁₀        cycloalkylalkylsulfinyl, C₄-C₁₀ cycloalkylalkylsulfonyl, C₂-C₈        alkenylthio, C₂-C₈ alkenylsulfinyl, C₂-C₈ alkenylsulfonyl, C₂-C₈        alkynylthio, C₂-C₈ alkynylsulfinyl or C₂-C₈ alkynylsulfonyl,        each unsubstituted or substituted with at least one substituent        independently selected from R¹⁷;    -   a is 1, 2 or 3;    -   each n is independently 0, 1 or 2; and    -   u and z in each instance of S(═O)_(u)(═NR²⁴)_(z) are        independently 0, 1 or 2, provided that the sum of u and z in        each instance of S(═O)_(u)(═NR²⁴)_(z) is 0, 1 or 2;    -   provided that when A is O, S, NCH₃ or C(R^(3c))═C(R^(3d)),        R^(3c) is H or F, and R^(3d) is H, F, CF₂H or CF₃, then at least        one of R^(3a) or R^(3b) is other than H.

Of note is that compounds of this invention are characterized byfavorable metabolic and/or soil residual patterns and exhibit activitycontrolling a spectrum of agronomic and nonagronomic invertebrate pests.

Of particular note, for reasons of invertebrate pest control spectrumand economic importance, protection of agronomic crops from damage orinjury caused by invertebrate pests by controlling invertebrate pestsare embodiments of the invention. Compounds of this invention because oftheir favorable translocation properties or systemicity in plants alsoprotect foliar or other plant parts which are not directly contactedwith a compound of Formula 1 or a composition comprising the compound.

Also noteworthy as embodiments of the present invention are compositionscomprising a compound of any of the preceding Embodiments, as well asany other embodiments described herein, and any combinations thereof,and at least one additional component selected from the group consistingof a surfactant, a solid diluent and a liquid diluent, said compositionsoptionally further comprising at least one additional biologicallyactive compound or agent.

Further noteworthy as embodiments of the present invention arecompositions for controlling an invertebrate pest comprising a compound(i.e. in a biologically effective amount) of any of the precedingEmbodiments, as well as any other embodiments described herein, and anycombinations thereof, and at least one additional component selectedfrom the group consisting of a surfactant, a solid diluent and a liquiddiluent, said compositions optionally further comprising at least oneadditional biologically active compound or agent (i.e. in a biologicallyeffective amount).

Embodiments of the invention also include a composition for protectingan animal comprising a compound (i.e. in a parasiticidally effectiveamount) of any of the preceding Embodiments and a carrier.

Embodiments of the invention further include methods for controlling aninvertebrate pest comprising contacting the invertebrate pest or itsenvironment with a biologically effective amount of a compound of any ofthe preceding Embodiments (e.g., as a composition described herein). Ofparticular note is a method for protecting an animal comprisingadministering to the animal a parasiticidally effective amount of acompound of any of the preceding Embodiments (e.g., as a compositiondescribed herein).

Embodiments of the invention also include a composition comprising acompound of any of the preceding Embodiments in the form of a soildrench liquid formulation. Embodiments of the invention further includemethods for controlling an invertebrate pest comprising contacting thesoil with a liquid composition as a soil drench comprising abiologically effective amount of a compound of any of the precedingEmbodiments.

Embodiments of the invention also include a spray composition forcontrolling an invertebrate pest comprising a compound (i.e. in abiologically effective amount) of any of the preceding Embodiments and apropellant. Embodiments of the invention further include a baitcomposition for controlling an invertebrate pest comprising a compound(i.e. in a biologically effective amount) of any of the precedingEmbodiments, one or more food materials, optionally an attractant, andoptionally a humectant. Embodiments of the invention also include adevice for controlling an invertebrate pest comprising said baitcomposition and a housing adapted to receive said bait composition,wherein the housing has at least one opening sized to permit theinvertebrate pest to pass through the opening so the invertebrate pestcan gain access to said bait composition from a location outside thehousing, and wherein the housing is further adapted to be placed in ornear a locus of potential or known activity for the invertebrate pest.

Embodiments of the invention also include a method for protecting a seedfrom an invertebrate pest comprising contacting the seed with abiologically effective amount of a compound of any of the precedingEmbodiments (e.g., as a composition described herein).

Embodiments of the invention also include methods for protecting ananimal from an invertebrate parasitic pest comprising administering tothe animal a parasiticidally effective amount of a compound of any ofthe preceding Embodiments.

Embodiments of the invention also include methods for controlling aninvertebrate pest comprising contacting the invertebrate pest or itsenvironment with a biologically effective amount of a compound ofFormula 1, an N-oxide, or a salt thereof, (e.g., as a compositiondescribed herein), provided that the methods are not methods of medicaltreatment of a human or animal body by therapy.

This invention also relates to such methods wherein the invertebratepest or its environment is contacted with a composition comprising abiologically effective amount of a compound of Formula 1, an N-oxide, ora salt thereof, and at least one additional component selected from thegroup consisting of surfactants, solid diluents and liquid diluents,said composition optionally further comprising a biologically effectiveamount of at least one additional biologically active compound or agent,provided that the methods are not methods of medical treatment of ahuman or animal body by therapy.

One or more of the following methods and variations as described inSchemes 1-13 can be used to prepare the compounds of Formula 1. Thedefinitions of R¹, R², R^(3a), R^(3b), R⁴, R⁵, X, Y, Z and A in thecompounds of Formulae 1-13 below are as defined above in the Summary ofthe Invention unless otherwise noted. Formulae 1a-1e are various subsetsof Formula 1, and all substituents for Formulae 1a-1e are as definedabove for Formula 1 unless otherwise indicated. Ambient or roomtemperature is defined as about 20-25° C.

Compounds of Formula 1a (i.e. Formula 1 wherein X and Y are O) can beprepared by condensation of appropriately substituted compounds ofFormula 2 with optionally substituted malonic acids (3a) in the presenceof condensing agents as shown in Scheme 1. Condensing agents can becarbodiimides such as dicyclohexyl carbodiimide (see, for example, Koch,A. et al. Tetrahedron 2004, 60, 10011-10018) or other agents well knownin the art to form amide bonds with or without activating agents such asN-hydroxybenzotriazole as described in Science of Synthesis 2005, 21,17-25 and Tetrahedron 2005, 61, 10827-10852. This reaction is typicallycarried out in an inert organic solvent, such as dichloromethane or1,2-dichloroethane, at temperatures from about 0 to about 80° C. for aperiod of 10 min to several days.

Compounds of Formula 1a can also be prepared by the condensation ofcompounds of Formula 2 with malonic acid esters (3b) wherein R is aC₁-C₅ alkyl group as shown in Scheme 2. These reactions can be performedneat or in the presence of inert solvents as described in Bulletin ofthe Chemical Society of Japan 1999, 72(3), 503-509. Inert solventsinclude, but are not limited to, high boiling hydrocarbons such asmesitylene, tetralin or cymene, or high boiling ethers such as diphenylether. Typical temperatures range from 50 to 250° C. Of note aretemperatures from 150 to 200° C., which typically provide rapid reactiontimes and high yields. These reactions can also be performed inmicrowave reactors within the same temperature ranges. Typical reactiontimes range from 5 minutes to several hours.

Compounds of Formula 3a can be prepared by a variety of methods known inthe art, for example by base hydrolysis of compounds of Formula 3b.

Compounds of Formula 3b wherein Z is a direct bond and R¹ is anoptionally substituted aromatic (including heteroaromatic) ring or ringsystem can be prepared by arylation of malonate esters (using compoundsof formula R¹X¹ wherein X¹ is Cl, Br or I, examples of which are foundin Tables I-24a-24c) catalyzed by palladium (J. Org. Chem. 2002, 67,541-555) or copper (Org. Lett. 2002, 4, 269-272 and Org. Lett. 2005, 7,4693-4695). Alternatively, compounds of Formula 3b can be prepared bythe method shown in Scheme 2a (see, for example, J. Med. Chem. 1982,25(6), 745-747).

Esters of Formula 4 can be prepared from the corresponding acids bymethods well known in the art. Many of the acids of Formula 4 where R isH are commercially available or readily prepared by methods known in theart (examples are listed in Table I-1).

Compounds of Formula 3b can also be prepared by the method shown inScheme 2b. Reaction of nitriles of Formula 3g with dialkyl carbonatesyields nitrile esters of Formula 3h, and subsequent acidic hydrolysis inthe presence of an alcohol provides the compounds of Formula 3b (see,for example, Helvetica Chimica Acta 1991, 74(2), 309-314). Many of thenitriles of Formula 3g are commercially available or readily prepared bymethods known in the art.

Compounds of Formula 1a can also be prepared by treatment of compoundsof Formula 2 with activated esters of Formula 3c wherein LvO is anactivated leaving group as shown in Scheme 3. Examples of Lv preferredfor ease of synthesis or reactivity are phenyl, 4-nitrophenyl orhalogen-substituted phenyl (e.g., 2,4,6-trichlorophenyl,pentachlorophenyl or pentafluorophenyl) as described in Archiv derPharmazie (Weinheim, Germany) 1991, 324, 863-866. Other activated estersare well known in the art and include, but are not limited to,N-hydroxysuccinimide esters (see, for example, J. Am. Chem. Soc. 2002,124, 6872-6878). Typical temperatures range from 50 to 200° C. Of noteare temperatures from 50 to 150° C., which typically provide rapidreaction times and high yields. These reactions can be performed with orwithout solvent, such as toluene, and in microwave reactors within thesame temperature ranges. Typical reaction times range from 5 minutes to2 hours.

Compounds of the Formula 3c can be prepared, for example, from compoundsof Formula 3a (see, for example, J. Het. Chem. 1980, 17, 337).

Compounds of Formula 1a can also be prepared by condensation ofcompounds of Formula 2 with compounds of Formula 3d or 3e, or bycondensation of compounds of Formula 2 with mixtures of compounds ofFormulae 3d and 3e as shown in Scheme 4. These reactions are typicallyperformed in an inert solvent, such as dichloromethane, and optionallyin the presence of two or more equivalents of an acid acceptor (see, forexample, Zeitschrift für Naturforschung, Teil B: Anorganische Chemie,Organische Chemie 1982, 37B(2), 222-233). Typical acid acceptorsinclude, but are not limited to, triethylamine,N,N-diisopropylethylamine, pyridine and substituted pyridines, and metalhydroxides, carbonates and bicarbonates.

Compounds of Formula 1b (i.e. Formula 1a wherein Z is a direct bond andR¹ is H) can be prepared by condensation of compounds of Formula 2 withcarbon suboxide (3f) (see, for example, J. Org. Chem. 1972, 37(9),1422-1425) as shown in Scheme 5. The reactions are typically performedin an inert solvent such as ether and can include the use of a catalystsuch as AlCl₃.

Compounds of Formula 2 can be prepared in a variety of ways known in theart; see, for example, Patai, S. The Chemistry of Functional Groups. TheChemistry of Amidines and Imidates; Wiley: Chichester, UK, 1975; TheChemistry of Amidines and Imidates; Patai, S.; Rappoport, Z., Eds.;Wiley: Chichester, UK, 1991; Vol. 2; Mega, T. et al. Bulletin of theChemical Society of Japan 1988, 61(12), 4315-4321; Ife, R. et al.European Journal of Medicinal Chemistry 1989, 24(3), 249-257; Wagaw, S.;Buchwald, S. Journal of Organic Chemistry 1996, 61(21), 7240-7241; Shen,Q. et al. Angewandte Chemie, International Edition 2005, 44(9),1371-1375; and Okano, K. et al. Organic Letters 2003, 5(26), 4987-4990.

One skilled in the art will recognize that the compounds of Formula 2can also be used as their acid-addition salts (e.g., hydrochloric salts,acetic acid salts) in the coupling methods of Schemes 1-5.

Compounds of Formula 1a wherein Z is a direct bond and R¹ is C₂-C₈alkenyl or an optionally substituted aromatic ring or ring system, canbe prepared from compounds of Formula 1c (i.e. Formula 1 wherein X and Yare O, Z is a direct bond and R¹ is Cl, Br or I, preferably Br or I) andcompounds of Formula 5 wherein R¹ is C₂-C₈ alkenyl or an optionallysubstituted aromatic ring or ring system, and M with Z—R¹ forms aboronic acid, boronic acid ester or trifluoroborate salt, or M istrialkylstannyl or zinc and Z is a direct bond, as shown in Scheme 6.

In a similar manner, compounds of Formula 1 wherein a substituent (e.g.,R¹ or R²) consists of two directly bonded aromatic rings or ring systems(e.g., a phenyl ring bonded to a second phenyl ring, a phenyl ringbonded to a pyridinyl ring, or a pyridinyl ring bonded to a secondpyridinyl ring) can be prepared by palladium-catalyzed coupling of thetwo appropriately substituted aromatic rings or ring systems. Thesepalladium-catalyzed couplings between an aromatic chloride, bromide oriodide and an aromatic boronic acid or ester, or an aromatic tin or zincreagent, are well known and have been extensively described in the art.For example, see Scheme 6a, wherein a compound of Formula 13a or 13b iscoupled with an appropriately substituted phenyl ring to provide thebiphenyl compound of Formula 13c. M is as defined above for Scheme 6.

These coupling reactions are typically carried out in the presence of apalladium catalyst and a base optionally under an inert atmosphere. Thepalladium catalysts used for these coupling reactions typicallycomprises palladium in a formal oxidation state of either 0 (i.e. Pd(0))or 2 (i.e. Pd(II)). A wide variety of such palladium-containingcompounds and complexes are useful as catalysts for these reactions.Examples of palladium-containing compounds and complexes useful ascatalysts in the methods include PdCl₂(PPh₃)₂(bis(triphenylphosphine)palladium (II) dichloride), Pd(PPh₃)₄(tetrakis(triphenylphosphine)palladium(0)), Pd(C₅H₇O₂)₂ (palladium(II)acetylacetonate), Pd₂(dba)₃ (tris(dibenzylidene-acetone)dipalladium(0)),and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II). Thesecoupling methods are generally conducted in a liquid phase, andtherefore the palladium catalyst preferably has good solubility in theliquid phase. Useful solvents include, for example, water, ethers suchas 1,2-dimethoxyethane, amides such as N,N-dimethylacetamide, andnon-halogenated aromatic hydrocarbons such as toluene.

The coupling methods can be conducted over a wide range of temperatures,ranging from about 25 to about 200° C. Of note are temperatures fromabout 60 to about 150° C., which typically provide fast reaction timesand high product yields. The general methods and procedures for Stille,Negishi and Suzuki couplings with aryl iodides, bromides or chloridesand an aryl tin, aryl zinc or aryl boronic acid respectively are wellknown in the literature; see, for example, E. Negishi, Handbook ofOrganopalladium Chemistry for Organic Synthesis, Wiley-Interscience,2002, New York, N.Y.

Compounds of Formula 1d (i.e. Formula 1 wherein X and Y are O and Z is adirect bond) wherein R¹ is an optionally substituted aromatic ring orring system can be prepared from compounds of Formula 1b (i.e. Formula1a wherein Z is a direct bond and R¹ is H) and compounds of Formula 6wherein X¹ is Cl, Br or I (preferably Br or I) as shown in Scheme 7.

These reactions are typically carried out in the presence of a copper orpalladium catalyst preferably under an inert atmosphere. The coppercatalysts used for the present method typically comprise copper inmetallic form (e.g., as a powder) or copper in a formal oxidation stateof 1 (i.e. Cu(I)). Examples of copper-containing compounds useful ascatalysts in the method of Scheme 7 include Cu, CuI, CuBr, CuCl.Examples of palladium-containing compounds useful as catalysts in themethod of Scheme 7 include Pd(OAc)₂. Useful solvents for the method ofScheme 7 include, for example, ethers such as 1,4-dioxane, amides suchas N,N-dimethylacetamide and dimethyl sulfoxide.

The method of Scheme 7 can be conducted over a wide range oftemperatures from 25 to 200° C. Of note are temperatures from 40 to 150°C. The method of Scheme 7 can be conducted in the presence of a ligand.A wide variety of copper-binding compounds are useful as ligands for thepresent method. Examples of useful ligands include, but are not limitedto, 1,10-phenanthroline, N,N-dimethylethylenediamine, L-proline and2-picolinic acid. The general methods and procedures forcopper-catalyzed Ullmann-type coupling reactions are well known in theliterature; see, for example, Xie, Ma, et al. Org. Lett. 2005, 7,4693-4695.

Compounds of Formula 1a wherein Z is S(O)_(n), C(═X¹) or C(═X¹)E can beprepared from compounds of Formula 1b by treatment with compounds ofFormula 7, optionally in the presence of a Lewis acid catalyst (e.g.,FeCl₃), as shown in Scheme 8. Examples of compounds of Formula 7 usefulin the method of Scheme 8 include, but are not limited to, sulfenyl andsulfonyl halides, carboxylic acids, acid anhydrides, acid halides,chloroformates, aminocarbonyl halides, isocyanates and isothiocyanates.Typically the reaction is performed in an inert solvent, more typicallya polar solvent such as N,N-dimethylacetamide or1-methyl-2-pyrrolidinone. The reaction is typically performed attemperatures from 0 to 180° C., more typically at ambient temperature to150° C. Microwave irradiation can be advantageous in heating thereaction mixture.

Compounds of the Formula 1e (i.e. Formula 1a wherein Z is C(═NOR⁸) orC(═NN(R⁶)₂) can be prepared by reacting compounds of Formula 1a whereinZ is C(═O) with an alkoxyamine or hydrazine salt of Formula 8, where X³is a counterion such as halide or oxalate, as shown in Scheme 9. Thereaction can be run in an alcoholic solvent such as ethanol or propanolat temperatures ranging from 80° C. to the reflux temperature of thesolvent in 3 to 24 hours.

Compounds of Formula 1d wherein R¹ is C₂-C₈ alkynyl, can be preparedfrom compounds of Formula 1c and substituted alkynes of Formula 9 by aSonogashira coupling reaction as shown in Scheme 10. Sonogashiracouplings are well known in the literature. See, for example, K.Sonogashira, Sonogashira Alkyne Synthesis Vol 2, p. 493 in E. Negishi,Handbook of Organopalladium Chemistry for Organic Synthesis,Wiley-Interscience, 2002, New York, N.Y.

Compounds of Formula 1c can be prepared from compounds of Formula 1b byhalogenation using, for example, liquid bromine or N-halosuccinimides(10) as shown in Scheme 11. Typically the reaction is performed in aninert solvent, more typically a halogenated solvent such as methylenechloride or 1,2-dichloroethane. The reaction is typically performed attemperatures from 0 to 80° C., more typically at ambient temperature.

Compounds of Formula 1a can also be prepared by alkylation of compoundsof Formula 11 using appropriately substituted alkylating agents andbases such as potassium carbonate as shown in Scheme 12 (see, forexample, Kappe, T. et al. Monatschefte fur Chemie 1971, 102, 412-424 andUrban, M. G.; Arnold, W. Helvetica Chimica Acta 1970, 53, 905-922).Alkylating agents include, but are not limited to, alkyl chlorides,bromides, iodides and sulfonate esters. A wide variety of bases andsolvents can be employed in the method of Scheme 12, and these bases andsolvents are well known in the art.

Compounds of Formula 11 can be prepared from compounds of Formula 2a bymethods analogous to those shown in Schemes 1 through 5 wherein thecompound of Formula 2 is replaced by a compound of Formula 2a. Compoundsof Formula 2a are commercially available or can be prepared by generalmethods well known in the art.

A particularly useful method for the preparation of compounds of Formula2 is shown in Scheme 13. In the method of Scheme 13, compounds ofFormula 2a are protected with suitable protecting groups such as, butnot limited to, tert-butoxycarbonyl, acetyl or formyl to form theintermediate of Formula 2b wherein PG is a protecting group. Thecompound of Formula 2b is then alkylated with an appropriate reagent ofFormula 12 (wherein at least one of R⁴ or R⁵ is hydrogen and X is aleaving group such as a halogen) to give an intermediate of Formula 2c.The protecting group is removed to provide a compound of Formula 2.Conditions for the formation and removal of protecting groups on anamine function are known in the literature (see, for example, Greene, T.W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.;Wiley: New York, 1991).

Examples of particularly useful compounds of Formula 2 are shown inTables I-27 to I-27g and I-29. Some examples of compounds of Formula 2aare shown in Tables I-28 to I-28g.

An alternative method for the preparation of compounds of Formula 2 isby the reductive amination of appropriate carbonyl compounds. Thismethod is shown in Steps B and C of Synthesis Example 1, and Step A ofSynthesis Example 5.

Another alternative method for the preparation of compounds of Formula 2is by the reaction of appropriately substituted amines withhalogen-substituted heteroaromatic compounds analogous to the compoundsof Formula 2a (i.e. compounds of Formula 2a wherein the amino group isreplaced with halogen) in the presence of a copper or palladiumcatalyst. This method is shown in Step A of Synthesis Example 2.

Compounds of Formula 2 can also be prepared in a variety of ways knownin the art; see, for example, Patai, S. The Chemistry of FunctionalGroups. The Chemistry of Amidines and Imidates; Wiley: Chichester, UK,1975; The Chemistry of Amidines and Imidates; Patai, S.; Rappoport, Z.,Eds.; Wiley: Chichester, UK, 1991; Vol. 2; Mega, T. et al. Bulletin ofthe Chemical Society of Japan 1988, 61(12), 4315-4321; Ife, R. et al.European Journal of Medicinal Chemistry 1989, 24(3), 249-257; Wagaw, S.;Buchwald, S. Journal of Organic Chemistry 1996, 61(21), 7240-7241; Shen,Q. et al. Angewandte Chemie, International Edition 2005, 44(9),1371-1375; and Okano, K. et al. Organic Letters 2003, 5(26), 4987-4990.

Compounds of Formula 1a wherein Z is O can be prepared by reaction ofappropriately substituted alcohols (e.g., alkyl alcohols or phenols)with compounds of Formula 1c in the presence of a Cu source (the Ullmannreaction; for example, see Hayashi, S.; Nakanishi, W. Bulletin of theChemical Society of Japan 2008, 81(12), 1605-1615). This Cu-catalyzedreaction is typically performed at room temperature to 200° C., moretypically at 100 to 150° C., and in a solvent such asN,N-dimethylformamide or N-methylpyrrolidinone. Alternatively, thismethod can be performed in the presence of a Pd source (for example, seeBuchwald, S. et al. Angew. Chem. Int. Ed. 2006, 45, 1-7. ThisPd-catalyzed reaction is typically performed at room temperature to 200°C., more typically at 100 to 150° C., and in the presence of a base suchas K₃PO₄, and in the presence of a ligand such as2-di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl (i.e.di-t-BuXphos) in an inert solvent such as toluene.

Compounds of Formula 1a wherein Z is NR⁶ can be prepared by reaction ofappropriately substituted amines (e.g., alkyl amines or anilines) withcompounds of Formula 1c in the presence of a Cu source (the Ullmannreaction; for example, see Xu, H.; Yin, K.; Huang, W. Chemistry—AEuropean Journal 2007, 13(36), 10281-10293). This Cu-catalyzed reactionis typically performed at room temperature to 200° C., more typically at100 to 150° C., and in a solvent such as N,N-dimethylformamide orN-methylpyrrolidinone. Alternatively, this method can be performed inthe presence of a Pd source (for example, see Uchiyama, M. et al. J. Am.Chem. Soc. 2004, 126(28), 8755-8759). This Pd-catalyzed reaction istypically performed at room temperature to 200° C., more typically at100 to 150° C., in an inert solvent such as toluene, and in the presenceof a base such as NaO-t-Bu.

Compounds of Formula 1 wherein X and/or Y are S can be prepared fromcorresponding compounds of Formula 1a by general methods known in theart involving treatment with thionating reagents such as P₄S₁₀ orLawessen's Reagent(2,4-bis-(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane 2,4-disulfide).Alternatively, malonic acids of Formula 3a can be treated withP₂S₆(CH₃)₂ as described in J. Am. Chem. Soc. 1988, 110 (4), 1316-1318.The resulting malonic acid sulfur derivatives can then be used toprepare the compounds of Formula 1 wherein X and/or Y are S by themethod of Scheme 1.

Schemes 1 through 13 illustrate methods to prepare compounds of Formula1 having a variety of substituents noted for R¹, R², R^(3a), R^(3b), R⁴,R⁵, X, Y, Z and A. Compounds of Formula 1 having R¹, R², R^(3a), R^(3b),R⁴, R⁵, X, Y, Z and A substituents other than those particularly notedfor Schemes 1 through 13 can be prepared by general methods known in theart of synthetic organic chemistry, including methods analogous to thosedescribed for Schemes 1 to 13.

Examples of intermediates useful in the preparation of compounds of thisinvention are shown in Tables I-1 through I-30. The followingabbreviations are used in the Tables which follow: Me means methyl, Etmeans ethyl, Pr means propyl, Ph means phenyl,C(O)O(2,4,6-trichlorophenyl) means

C(O)O(4-nitrophenyl) means

andC(O)(3-methyl-2-pyridinylamino) means

TABLE I-1

R^(x) is C(O)OH; R^(y) is H; R^(b), R^(c), R^(d) and R^(e) are H R^(a) HF Cl Br I Me Et Pr i-Pr c-Pr t-Bu CF₃ CH₂F CHF₂ OMe OEt O—n-Pr OPhCH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂ OCH₂C≡CH O—c-Pr OCF₃ OCHF₂ OCH₂CF₃SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Et cyano C(O)NHMe C(O)NMe₂C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl 3-chlorophenyl 3-(CF₃)phenyl3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl 4-fluorophenyl4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(x) is C(O)OH; R^(y) is H; R^(a),R^(c), R^(d) and R^(e) are H R^(b) H F Cl Br I Me Et Pr i-Pr c-Pr t-BuCF₃ CH₂F CHF₂ OMe OEt O—n-Pr OPh CH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂OCH₂C≡CH O—c-Pr OCF₃ OCHF₂ OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂MeCO₂Et cyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl3-chlorophenyl 3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl4-fluorophenyl 4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(x) is C(O)OH; R^(y) is H; R^(a),R^(b), R^(d) and R^(e) are H R^(c) H F Cl Br I Me Et Pr i-Pr c-Pr t-BuCF₃ CH₂F CHF₂ OMe OEt O—n-Pr OPh CH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂OCH₂C≡CH O—c-Pr OCF₃ OCHF₂ OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂MeCO₂Et cyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl3-chlorophenyl 3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl4-fluorophenyl 4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(x) is C(O)OH; R^(y) is H; R^(a) isF; R^(c), R^(d) and R^(e) are H R^(b) H F Cl Br I Me Et Pr i-Pr c-Prt-Bu CF₃ CH₂F CHF₂ OMe OEt O—n-Pr OPh CH═CH₂ C≡CH phenyl O—i-PrOCH₂CH═CH₂ OCH₂C≡CH O—c-Pr OCF₃ OCHF₂ OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃SO₂CF₃ CO₂Me CO₂Et cyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me C(═NOEt)Me2-fluorophenyl 3-chlorophenyl 3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl3-(OCF₃)phenyl 4-fluorophenyl 4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl4-bromophenyl 6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl6-(CF₃)-3-pyridinyl 4,6-dichloro-3-pyridinyl2-fluoro-6-chloro-3-pyridinyl 2,6-dichloro-3-pyridinyl2-bromo-5-chloro-4-pyridinyl 3-bromo-5-fluorophenyl3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl 2,4-dichlorophenyl2,4-difluorophenyl 2-fluoro-4-cyanophenyl 2-fluoro-4-chlorophenyl2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl 2,4-bis(CF₃)phenyl2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl 2-(CF₃)-4-fluorophenyl2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl 2-(CF₃)-4-chlorophenyl2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl 2-fluoro-5-chlorophenyl2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl 2-chloro-5-(CF₃)phenylN-Me-4-pyrazolyl 3-Me-5-isoxazolyl 6-(6-Cl-3-pyridinyl)-3-pyridinylR^(x) is C(O)OH; R^(y) is H; R^(a) is F; R^(b), R^(d) and R^(e) are HR^(c) H F Cl Br I Me Et Pr i-Pr c-Pr t-Bu CF₃ CH₂F CHF₂ OMe OEt O—n-PrOPh CH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂ OCH₂C≡CH O—c-Pr OCF₃ OCHF₂OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Et cyano C(O)NHMeC(O)NMe₂ C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl 3-chlorophenyl3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl 4-fluorophenyl4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(x) is C(O)OH; R^(y) is H; R^(a) isF; R^(b), R^(c) and R^(e) are H R^(d) H F Cl Br I Me Et Pr i-Pr c-Prt-Bu CF₃ CH₂F CHF₂ OMe OEt O—n-Pr OPh CH═CH₂ C≡CH phenyl O—i-PrOCH₂CH═CH₂ OCH₂C≡CH O—c-Pr OCF₃ OCHF₂ OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃SO₂CF₃ CO2Me CO₂Et cyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me C(═NOEt)Me2-fluorophenyl 3-chlorophenyl 3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl3-(OCF₃)phenyl 4-fluorophenyl 4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl4-bromophenyl 6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl6-(CF₃)-3-pyridinyl 4,6-dichloro-3-pyridinyl2-fluoro-6-chloro-3-pyridinyl 2,6-dichloro-3-pyridinyl2-bromo-5-chloro-4-pyridinyl 3-bromo-5-fluorophenyl3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl 2,4-dichlorophenyl2,4-difluorophenyl 2-fluoro-4-cyanophenyl 2-fluoro-4-chlorophenyl2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl 2,4-bis(CF₃)phenyl2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl 2-(CF₃)-4-fluorophenyl2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl 2-(CF₃)-4-chlorophenyl2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl 2-fluoro-5-chlorophenyl2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl 2-chloro-5-(CF₃)phenylN-Me-4-pyrazolyl 3-Me-5-isoxazolyl 6-(6-Cl-3-pyridinyl)-3-pyridinylR^(x) is C(O)OH; R^(y) is H; R^(a) is F; R^(b), R^(c) and R^(d) are HR^(e) H F Cl Br I Me Et Pr i-Pr c-Pr t-Bu CF₃ CH₂F CHF₂ OMe OEt O—n-PrOPh CH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂ OCH₂C≡CH O—c-Pr OCF₃ OCHF₂OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Et cyano C(O)NHMeC(O)NMe₂ C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl 3-chlorophenyl3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl 4-fluorophenyl4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(x) is C(O)OH; R^(y) is H; R^(a) isCl; R^(c), R^(d) and R^(e) are H R^(b) H F Cl Br I Me Et Pr i-Pr c-Prt-Bu CF₃ CH₂F CHF₂ OMe OEt O—n-Pr OPh CH═CH₂ C≡CH phenyl O—i-PrOCH₂CH═CH₂ OCH₂C≡CH O—c-Pr OCF₃ OCHF₂ OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃SO₂CF₃ CO₂Me CO₂Et cyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me C(═NOEt)Me2-fluorophenyl 3-chlorophenyl 3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl3-(OCF₃)phenyl 4-fluorophenyl 4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl4-bromophenyl 6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl6-(CF₃)-3-pyridinyl 4,6-dichloro-3-pyridinyl2-fluoro-6-chloro-3-pyridinyl 2,6-dichloro-3-pyridinyl2-bromo-5-chloro-4-pyridinyl 3-bromo-5-fluorophenyl3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl 2,4-dichlorophenyl2,4-difluorophenyl 2-fluoro-4-cyanophenyl 2-fluoro-4-chlorophenyl2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl 2,4-bis(CF₃)phenyl2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl 2-(CF₃)-4-fluorophenyl2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl 2-(CF₃)-4-chlorophenyl2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl 2-fluoro-5-chlorophenyl2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl 2-chloro-5-(CF₃)phenylN-Me-4-pyrazolyl 3-Me-5-isoxazolyl 6-(6-Cl-3-pyridinyl)-3-pyridinylR^(x) is C(O)OH; R^(y) is H; R^(a) is Cl; R^(b), R^(d) and R^(e) are HR^(c) H F Cl Br I Me Et Pr i-Pr c-Pr t-Bu CF₃ CH₂F CHF₂ OMe OEt O—n-PrOPh CH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂ OCH₂C≡CH O—c-Pr OCF₃ OCHF₂OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Et cyano C(O)NHMeC(O)NMe₂ C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl 3-chlorophenyl3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl 4-fluorophenyl4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(x) is C(O)OH; R^(y) is H; R^(a) isCl; R^(b), R^(c) and R^(e) are H R^(d) H F Cl Br I Me Et Pr i-Pr c-Prt-Bu CF₃ CH₂F CHF₂ OMe OEt O—n-Pr OPh CH═CH₂ C≡CH phenyl O—i-PrOCH₂CH═CH₂ OCH₂C≡CH O—c-Pr OCF₃ OCHF₂ OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃SO₂CF₃ CO₂Me CO₂Et cyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me C(═NOEt)Me2-fluorophenyl 3-chlorophenyl 3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl3-(OCF₃)phenyl 4-fluorophenyl 4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl4-bromophenyl 6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl6-(CF₃)-3-pyridinyl 4,6-dichloro-3-pyridinyl2-fluoro-6-chloro-3-pyridinyl 2,6-dichloro-3-pyridinyl2-bromo-5-chloro-4-pyridinyl 3-bromo-5-fluorophenyl3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl 2,4-dichlorophenyl2,4-difluorophenyl 2-fluoro-4-cyanophenyl 2-fluoro-4-chlorophenyl2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl 2,4-bis(CF₃)phenyl2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl 2-(CF₃)-4-fluorophenyl2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl 2-(CF₃)-4-chlorophenyl2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl 2-fluoro-5-chlorophenyl2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl 2-chloro-5-(CF₃)phenylN-Me-4-pyrazolyl 3-Me-5-isoxazolyl 6-(6-Cl-3-pyridinyl)-3-pyridinylR^(x) is C(O)OH; R^(y) is H; R^(a) is Cl; R^(b), R^(c) and R^(d) are HR^(e) H F Cl Br I Me Et Pr i-Pr c-Pr t-Bu CF₃ CH₂F CHF₂ OMe OEt O—n-PrOPh CH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂ OCH₂C≡CH O—c-Pr OCF₃ OCHF₂OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Et cyano C(O)NHMeC(O)NMe₂ C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl 3-chlorophenyl3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl 4-fluorophenyl4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(x) is C(O)OH; R^(y) is H; R^(a) isOMe; R^(c), R^(d) and R^(e) are H R^(b) H F Cl Br I Me Et Pr i-Pr c-Prt-Bu CF₃ CH₂F CHF₂ OMe OEt O—n-Pr OPh CH═CH₂ C≡CH phenyl O—i-PrOCH₂CH═CH₂ OCH₂C≡CH O—c-Pr OCF₃ OCHF₂ OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃SO₂CF₃ CO₂Me CO₂Et cyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me C(═NOEt)Me2-fluorophenyl 3-chlorophenyl 3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl3-(OCF₃)phenyl 4-fluorophenyl 4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl4-bromophenyl 6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl6-(CF₃)-3-pyridinyl 4,6-dichloro-3-pyridinyl2-fluoro-6-chloro-3-pyridinyl 2,6-dichloro-3-pyridinyl2-bromo-5-chloro-4-pyridinyl 3-bromo-5-fluorophenyl3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl 2,4-dichlorophenyl2,4-difluorophenyl 2-fluoro-4-cyanophenyl 2-fluoro-4-chlorophenyl2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl 2,4-bis(CF₃)phenyl2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl 2-(CF₃)-4-fluorophenyl2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl 2-(CF₃)-4-chlorophenyl2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl 2-fluoro-5-chlorophenyl2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl 2-chloro-5-(CF₃)phenylN-Me-4-pyrazolyl 3-Me-5-isoxazolyl 6-(6-Cl-3-pyridinyl)-3-pyridinylR^(x) is C(O)OH; R^(y) is H; R^(a) is OMe; R^(b), R^(d) and R^(e) are HR^(c) H F Cl Br I Me Et Pr i-Pr c-Pr t-Bu CF₃ CH₂F CHF₂ OMe OEt O—n-PrOPh CH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂ OCH₂C≡CH O—c-Pr OCF₃ OCHF₂OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Et cyano C(O)NHMeC(O)NMe₂ C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl 3-chlorophenyl3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl 4-fluorophenyl4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(x) is C(O)OH; R^(y) is H; R^(a) isOMe; R^(b), R^(c) and R^(e) are H R^(d) H F Cl Br I Me Et Pr i-Pr c-Prt-Bu CF₃ CH₂F CHF₂ OMe OEt O—n-Pr OPh CH═CH₂ C≡CH phenyl O—i-PrOCH₂CH═CH₂ OCH₂C≡CH O—c-Pr OCF₃ OCHF₂ OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃SO₂CF₃ CO₂Me CO₂Et cyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me C(═NOEt)Me2-fluorophenyl 3-chlorophenyl 3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl3-(OCF₃)phenyl 4-fluorophenyl 4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl4-bromophenyl 6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl6-(CF₃)-3-pyridinyl 4,6-dichloro-3-pyridinyl2-fluoro-6-chloro-3-pyridinyl 2,6-dichloro-3-pyridinyl2-bromo-5-chloro-4-pyridinyl 3-bromo-5-fluorophenyl3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl 2,4-dichlorophenyl2,4-difluorophenyl 2-fluoro-4-cyanophenyl 2-fluoro-4-chlorophenyl2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl 2,4-bis(CF₃)phenyl2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl 2-(CF₃)-4-fluorophenyl2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl 2-(CF₃)-4-chlorophenyl2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl 2-fluoro-5-chlorophenyl2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl 2-chloro-5-(CF₃)phenylN-Me-4-pyrazolyl 3-Me-5-isoxazolyl 6-(6-Cl-3-pyridinyl)-3-pyridinylR^(x) is C(O)OH; R^(y) is H; R^(a) is OMe; R^(b), R^(c) and R^(d) are HR^(e) H F Cl Br I Me Et Pr i-Pr c-Pr t-Bu CF₃ CH₂F CHF₂ OMe OEt O—n-PrOPh CH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂ OCH₂C≡CH O—c-Pr OCF₃ OCHF₂OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Et cyano C(O)NHMeC(O)NMe₂ C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl 3-chlorophenyl3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl 4-fluorophenyl4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(x) is C(O)OH; R^(y) is H; R^(a) isMe; R^(c), R^(d) and R^(e) are H R^(b) H F Cl Br I Me Et Pr i-Pr c-Prt-Bu CF₃ CH₂F CHF₂ OMe OEt O—n-Pr OPh CH═CH₂ C≡CH phenyl O—i-PrOCH₂CH═CH₂ OCH₂C≡CH O—c-Pr OCF₃ OCHF₂ OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃SO₂CF₃ CO₂Me CO₂Et cyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me C(═NOEt)Me2-fluorophenyl 3-chlorophenyl 3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl3-(OCF₃)phenyl 4-fluorophenyl 4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl4-bromophenyl 6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl6-(CF₃)-3-pyridinyl 4,6-dichloro-3-pyridinyl2-fluoro-6-chloro-3-pyridinyl 2,6-dichloro-3-pyridinyl2-bromo-5-chloro-4-pyridinyl 3-bromo-5-fluorophenyl3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl 2,4-dichlorophenyl2,4-difluorophenyl 2-fluoro-4-cyanophenyl 2-fluoro-4-chlorophenyl2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl 2,4-bis(CF₃)phenyl2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl 2-(CF₃)-4-fluorophenyl2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl 2-(CF₃)-4-chlorophenyl2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl 2-fluoro-5-chlorophenyl2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl 2-chloro-5-(CF₃)phenylN-Me-4-pyrazolyl 3-Me-5-isoxazolyl 6-(6-Cl-3-pyridinyl)-3-pyridinylR^(x) is C(O)OH; R^(y) is H; R^(a) is Me; R^(b), R^(d) and R^(e) are HR^(c) H F Cl Br I Me Et Pr i-Pr c-Pr t-Bu CF₃ CH₂F CHF₂ OMe OEt O—n-PrOPh CH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂ OCH₂C≡CH O—c-Pr OCF₃ OCHF₂OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Et cyano C(O)NHMeC(O)NMe₂ C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl 3-chlorophenyl3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl 4-fluorophenyl4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(x) is C(O)OH; R^(y) is H; R^(a) isMe; R^(b), R^(c) and R^(e) are H R^(d) H F Cl Br I Me Et Pr i-Pr c-Prt-Bu CF₃ CH₂F CHF₂ OMe OEt O—n-Pr OPh CH═CH₂ C≡CH phenyl O—i-PrOCH₂CH═CH₂ OCH₂C≡CH O—c-Pr OCF₃ OCHF₂ OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃SO₂CF₃ CO₂Me CO₂Et cyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me C(═NOEt)Me2-fluorophenyl 3-chlorophenyl 3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl3-(OCF₃)phenyl 4-fluorophenyl 4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl4-bromophenyl 6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl6-(CF₃)-3-pyridinyl 4,6-dichloro-3-pyridinyl2-fluoro-6-chloro-3-pyridinyl 2,6-dichloro-3-pyridinyl2-bromo-5-chloro-4-pyridinyl 3-bromo-5-fluorophenyl3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl 2,4-dichlorophenyl2,4-difluorophenyl 2-fluoro-4-cyanophenyl 2-fluoro-4-chlorophenyl2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl 2,4-bis(CF₃)phenyl2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl 2-(CF₃)-4-fluorophenyl2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl 2-(CF₃)-4-chlorophenyl2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl 2-fluoro-5-chlorophenyl2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl 2-chloro-5-(CF₃)phenylN-Me-4-pyrazolyl 3-Me-5-isoxazolyl 6-(6-Cl-3-pyridinyl)-3-pyridinylR^(x) is C(O)OH; R^(y) is H; R^(a) is Me; R^(b), R^(c) and R^(d) are HR^(e) H F Cl Br I Me Et Pr i-Pr c-Pr t-Bu CF₃ CH₂F CHF₂ OMe OEt O—n-PrOPh CH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂ OCH₂C≡CH O—c-Pr OCF₃ OCHF₂OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Et cyano C(O)NHMeC(O)NMe₂ C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl 3-chlorophenyl3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl 4-fluorophenyl4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(x) is C(O)OH; R^(y) is H; R^(d) isCl; R^(a), R^(c) and R^(e) are H R^(b) H F Cl Br I Me Et Pr i-Pr c-Prt-Bu CF₃ CH₂F CHF₂ OMe OEt O—n-Pr OPh CH═CH₂ C≡CH phenyl O—i-PrOCH₂CH═CH₂ OCH₂C≡CH O—c-Pr OCF₃ OCHF₂ OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃SO₂CF₃ CO₂Me CO₂Et cyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me C(═NOEt)Me2-fluorophenyl 3-chlorophenyl 3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl3-(OCF₃)phenyl 4-fluorophenyl 4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl4-bromophenyl 6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl6-(CF₃)-3-pyridinyl 4,6-dichloro-3-pyridinyl2-fluoro-6-chloro-3-pyridinyl 2,6-dichloro-3-pyridinyl2-bromo-5-chloro-4-pyridinyl 3-bromo-5-fluorophenyl3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl 2,4-dichlorophenyl2,4-difluorophenyl 2-fluoro-4-cyanophenyl 2-fluoro-4-chlorophenyl2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl 2,4-bis(CF₃)phenyl2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl 2-(CF₃)-4-fluorophenyl2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl 2-(CF₃)-4-chlorophenyl2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl 2-fluoro-5-chlorophenyl2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl 2-chloro-5-(CF₃)phenylN-Me-4-pyrazolyl 3-Me-5-isoxazolyl 6-(6-Cl-3-pyridinyl)-3-pyridinylR^(x) is C(O)OH; R^(y) is H; R^(d) is CF₃; R^(a), R^(c) and R^(e) are HR^(b) H F Cl Br I Me Et Pr i-Pr c-Pr t-Bu CF₃ CH₂F CHF₂ OMe OEt O—n-PrOPh CH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂ OCH₂C≡CH O—c-Pr OCF₃ OCHF₂OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Et cyano C(O)NHMeC(O)NMe₂ C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl 3-chlorophenyl3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl 4-fluorophenyl4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(x) is C(O)OH; R^(y) is H; R^(b) isBr; R^(a), R^(c) and R^(e) are H R^(d) H F Cl Br I Me Et Pr i-Pr c-Prt-Bu CF₃ CH₂F CHF₂ OMe OEt O—n-Pr OPh CH═CH₂ C≡CH phenyl O—i-PrOCH₂CH═CH₂ OCH₂C≡CH O—c-Pr OCF₃ OCHF₂ OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃SO₂CF₃ CO₂Me CO₂Et cyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me C(═NOEt)Me2-fluorophenyl 3-chlorophenyl 3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl3-(OCF₃)phenyl 4-fluorophenyl 4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl4-bromophenyl 6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl6-(CF₃)-3-pyridinyl 4,6-dichloro-3-pyridinyl2-fluoro-6-chloro-3-pyridinyl 2,6-dichloro-3-pyridinyl2-bromo-5-chloro-4-pyridinyl 3-bromo-5-fluorophenyl3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl 2,4-dichlorophenyl2,4-difluorophenyl 2-fluoro-4-cyanophenyl 2-fluoro-4-chlorophenyl2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl 2,4-bis(CF₃)phenyl2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl 2-(CF₃)-4-fluorophenyl2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl 2-(CF₃)-4-chlorophenyl2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl 2-fluoro-5-chlorophenyl2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl 2-chloro-5-(CF₃)phenylN-Me-4-pyrazolyl 3-Me-5-isoxazolyl 6-(6-Cl-3-pyridinyl)-3-pyridinylR^(x) is C(O)OH; R^(y) is H; R^(b) is OCF₃; R^(a), R^(c) and R^(e) are HR^(d) H F Cl Br I Me Et Pr i-Pr c-Pr t-Bu CF₃ CH₂F CHF₂ OMe OEt O—n-PrOPh CH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂ OCH₂C≡CH O—c-Pr OCF₃ OCHF₂OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Et cyano C(O)NHMeC(O)NMe₂ C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl 3-chlorophenyl3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl 4-fluorophenyl4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(x) is C(O)OH; R^(y) is H; R^(b) isOMe; R^(a), R^(c) and R^(e) are H R^(d) H F Cl Br I Me Et Pr i-Pr c-Prt-Bu CF₃ CH₂F CHF₂ OMe OEt O—n-Pr OPh CH═CH₂ C≡CH phenyl O—i-PrOCH₂CH═CH₂ OCH₂C≡CH O—c-Pr OCF₃ OCHF₂ OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃SO₂CF₃ CO₂Me CO₂Et cyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me C(═NOEt)Me2-fluorophenyl 3-chlorophenyl 3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl3-(OCF₃)phenyl 4-fluorophenyl 4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl4-bromophenyl 6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl6-(CF₃)-3-pyridinyl 4,6-dichloro-3-pyridinyl2-fluoro-6-chloro-3-pyridinyl 2,6-dichloro-3-pyridinyl2-bromo-5-chloro-4-pyridinyl 3-bromo-5-fluorophenyl3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl 2,4-dichlorophenyl2,4-difluorophenyl 2-fluoro-4-cyanophenyl 2-fluoro-4-chlorophenyl2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl 2,4-bis(CF₃)phenyl2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl 2-(CF₃)-4-fluorophenyl2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl 2-(CF₃)-4-chlorophenyl2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl 2-fluoro-5-chlorophenyl2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl 2-chloro-5-(CF₃)phenylN-Me-4-pyrazolyl 3-Me-5-isoxazolyl 6-(6-Cl-3-pyridinyl)-3-pyridinylR^(x) is C(O)OH; R^(y) is H; R^(b) is F; R^(a), R^(c) and R^(e) are HR^(d) H F Cl Br I Me Et Pr i-Pr c-Pr t-Bu CF₃ CH₂F CHF₂ OMe OEt O—n-PrOPh CH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂ OCH₂C≡CH O—c-Pr OCF₃ OCHF₂OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Et cyano C(O)NHMeC(O)NMe₂ C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl 3-chlorophenyl3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl 4-fluorophenyl4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(x) is C(O)OH; R^(y) is H; R^(b) isCN; R^(a), R^(c) and R^(e) are H R^(d) H F Cl Br I Me Et Pr i-Pr c-Prt-Bu CF₃ CH₂F CHF₂ OMe OEt O—n-Pr OPh CH═CH₂ C≡CH phenyl O—i-PrOCH₂CH═CH₂ OCH₂C≡CH O—c-Pr OCF₃ OCHF₂ OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃SO₂CF₃ CO₂Me CO₂Et cyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me C(═NOEt)Me2-fluorophenyl 3-chlorophenyl 3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl3-(OCF₃)phenyl 4-fluorophenyl 4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl4-bromophenyl 6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl6-(CF₃)-3-pyridinyl 4,6-dichloro-3-pyridinyl2-fluoro-6-chloro-3-pyridinyl 2,6-dichloro-3-pyridinyl2-bromo-5-chloro-4-pyridinyl 3-bromo-5-fluorophenyl3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl 2,4-dichlorophenyl2,4-difluorophenyl 2-fluoro-4-cyanophenyl 2-fluoro-4-chlorophenyl2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl 2,4-bis(CF₃)phenyl2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl 2-(CF₃)-4-fluorophenyl2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl 2-(CF₃)-4-chlorophenyl2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl 2-fluoro-5-chlorophenyl2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl 2-chloro-5-(CF₃)phenylN-Me-4-pyrazolyl 3-Me-5-isoxazolyl 6-(6-Cl-3-pyridinyl)-3-pyridinylR^(x) is C(O)OH; R^(y) is H; R^(b) is Me; R^(a), R^(c) and R^(e) are HR^(d) H F Cl Br I Me Et Pr i-Pr c-Pr t-Bu CF₃ CH₂F CHF₂ OMe OEt O—n-PrOPh CH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂ OCH₂C≡CH O—c-Pr OCF₃ OCHF₂OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Et cyano C(O)NHMeC(O)NMe₂ C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl 3-chlorophenyl3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl 4-fluorophenyl4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(x) is C(O)OH; R^(y) is H; R^(b) isI; R^(a), R^(c) and R^(e) are H R^(d) H F Cl Br I Me Et Pr i-Pr c-Prt-Bu CF₃ CH₂F CHF₂ OMe OEt O—n-Pr OPh CH═CH₂ C≡CH phenyl O—i-PrOCH₂CH═CH₂ OCH₂C≡CH O—c-Pr OCF₃ OCHF₂ OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃SO₂CF₃ CO₂Me CO₂Et cyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me C(═NOEt)Me2-fluorophenyl 3-chlorophenyl 3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl3-(OCF₃)phenyl 4-fluorophenyl 4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl4-bromophenyl 6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl6-(CF₃)-3-pyridinyl 4,6-dichloro-3-pyridinyl2-fluoro-6-chloro-3-pyridinyl 2,6-dichloro-3-pyridinyl2-bromo-5-chloro-4-pyridinyl 3-bromo-5-fluorophenyl3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl 2,4-dichlorophenyl2,4-difluorophenyl 2-fluoro-4-cyanophenyl 2-fluoro-4-chlorophenyl2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl 2,4-bis(CF₃)phenyl2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl 2-(CF₃)-4-fluorophenyl2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl 2-(CF₃)-4-chlorophenyl2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl 2-fluoro-5-chlorophenyl2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl 2-chloro-5-(CF₃)phenylN-Me-4-pyrazolyl 3-Me-5-isoxazolyl 6-(6-Cl-3-pyridinyl)-3-pyridinylR^(x) is C(O)OH; R^(y) is H; R^(a) and R^(b) are F; R^(c) and R^(e) areH R^(d) H F Cl Br I Me Et Pr i-Pr c-Pr t-Bu CF₃ CH₂F CHF₂ OMe OEt O—n-PrOPh CH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂ OCH₂C≡CH O—c-Pr OCF₃ OCHF₂OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Et cyano C(O)NHMeC(O)NMe₂ C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl 3-chlorophenyl3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl 4-fluorophenyl4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(x) is C(O)OH; R^(y) is H; R^(a) isF; R^(b) is Cl; R^(c) and R^(e) are H R^(d) H F Cl Br I Me Et Pr i-Prc-Pr t-Bu CF₃ CH₂F CHF₂ OMe OEt O—n-Pr OPh CH═CH₂ C≡CH phenyl O—i-PrOCH₂CH═CH₂ OCH₂C≡CH O—c-Pr OCF₃ OCHF₂ OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃SO₂CF₃ CO₂Me CO₂Et cyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me C(═NOEt)Me2-fluorophenyl 3-chlorophenyl 3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl3-(OCF₃)phenyl 4-fluorophenyl 4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl4-bromophenyl 6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl6-(CF₃)-3-pyridinyl 4,6-dichloro-3-pyridinyl2-fluoro-6-chloro-3-pyridinyl 2,6-dichloro-3-pyridinyl2-bromo-5-chloro-4-pyridinyl 3-bromo-5-fluorophenyl3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl 2,4-dichlorophenyl2,4-difluorophenyl 2-fluoro-4-cyanophenyl 2-fluoro-4-chlorophenyl2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl 2,4-bis(CF₃)phenyl2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl 2-(CF₃)-4-fluorophenyl2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl 2-(CF₃)-4-chlorophenyl2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl 2-fluoro-5-chlorophenyl2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl 2-chloro-5-(CF₃)phenylN-Me-4-pyrazolyl 3-Me-5-isoxazolyl 6-(6-Cl-3-pyridinyl)-3-pyridinylR^(x) is C(O)OH; R^(y) is H; R^(c) is OMe; R^(a), R^(b) and R^(e) are HR^(d) H F Cl Br I Me Et Pr i-Pr c-Pr t-Bu CF₃ CH₂F CHF₂ OMe OEt O—n-PrOPh CH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂ OCH₂C≡CH O—c-Pr OCF₃ OCHF₂OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Et cyano C(O)NHMeC(O)NMe₂ C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl 3-chlorophenyl3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl 4-fluorophenyl4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(x) is C(O)OH; R^(y) is H; R^(c) isMe; R^(a), R^(b) and R^(e) are H R^(d) H F Cl Br I Me Et Pr i-Pr c-Prt-Bu CF₃ CH₂F CHF₂ OMe OEt O—n-Pr OPh CH═CH₂ C≡CH phenyl O—i-PrOCH₂CH═CH₂ OCH₂C≡CH O—c-Pr OCF₃ OCHF₂ OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃SO₂CF₃ CO₂Me CO₂Et cyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me C(═NOEt)Me2-fluorophenyl 3-chlorophenyl 3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl3-(OCF₃)phenyl 4-fluorophenyl 4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl4-bromophenyl 6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl6-(CF₃)-3-pyridinyl 4,6-dichloro-3-pyridinyl2-fluoro-6-chloro-3-pyridinyl 2,6-dichloro-3-pyridinyl2-bromo-5-chloro-4-pyridinyl 3-bromo-5-fluorophenyl3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl 2,4-dichlorophenyl2,4-difluorophenyl 2-fluoro-4-cyanophenyl 2-fluoro-4-chlorophenyl2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl 2,4-bis(CF₃)phenyl2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl 2-(CF₃)-4-fluorophenyl2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl 2-(CF₃)-4-chlorophenyl2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl 2-fluoro-5-chlorophenyl2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl 2-chloro-5-(CF₃)phenylN-Me-4-pyrazolyl 3-Me-5-isoxazolyl 6-(6-Cl-3-pyridinyl)-3-pyridinylR^(x) is C(O)OH; R^(y) is H; R^(c) is F; R^(a), R^(b) and R^(e) are HR^(d) H F Cl Br I Me Et Pr i-Pr c-Pr t-Bu CF₃ CH₂F CHF₂ OMe OEt O—n-PrOPh CH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂ OCH₂C≡CH O—c-Pr OCF₃ OCHF₂OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Et cyano C(O)NHMeC(O)NMe₂ C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl 3-chlorophenyl3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl 4-fluorophenyl4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(x) is C(O)OH; R^(y) is H; R^(c) isCl; R^(a), R^(b) and R^(e) are H R^(d) H F Cl Br I Me Et Pr i-Pr c-Prt-Bu CF₃ CH₂F CHF₂ OMe OEt O—n-Pr OPh CH═CH₂ C≡CH phenyl O—i-PrOCH₂CH═CH₂ OCH₂C≡CH O—c-Pr OCF₃ OCHF₂ OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃SO₂CF₃ CO₂Me CO₂Et cyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me C(═NOEt)Me2-fluorophenyl 3-chlorophenyl 3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl3-(OCF₃)phenyl 4-fluorophenyl 4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl4-bromophenyl 6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl6-(CF₃)-3-pyridinyl 4,6-dichloro-3-pyridinyl2-fluoro-6-chloro-3-pyridinyl 2,6-dichloro-3-pyridinyl2-bromo-5-chloro-4-pyridinyl 3-bromo-5-fluorophenyl3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl 2,4-dichlorophenyl2,4-difluorophenyl 2-fluoro-4-cyanophenyl 2-fluoro-4-chlorophenyl2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl 2,4-bis(CF₃)phenyl2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl 2-(CF₃)-4-fluorophenyl2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl 2-(CF₃)-4-chlorophenyl2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl 2-fluoro-5-chlorophenyl2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl 2-chloro-5-(CF₃)phenylN-Me-4-pyrazolyl 3-Me-5-isoxazolyl 6-(6-Cl-3-pyridinyl)-3-pyridinylR^(x) is C(O)OH; R^(y) is H; R^(a) and R^(e) are F; R^(c) and R^(d) areH R^(b) H F Cl Br I Me Et Pr i-Pr c-Pr t-Bu CF₃ CH₂F CHF₂ OMe OEt O—n-PrOPh CH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂ OCH₂C≡CH O—c-Pr OCF₃ OCHF₂OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Et cyano C(O)NHMeC(O)NMe₂ C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl 3-chlorophenyl3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl 4-fluorophenyl4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl

Table I-2

Table I-2 is identical to Table I-1, except that R^(x) is C(O)OMe.

Table I-3

Table I-3 is identical to Table I-1, except that R^(x) is C(O)OEt.

Table I-4

Table I-4 is identical to Table I-1, except that R^(x) is C(O)OPh.

Table I-5

Table I-5 is identical to Table I-1, except that R^(x) is C(O)OC(CH₃)₃.

Table I-5a

Table I-5a is identical to Table I-1, except that R^(x) isC(O)O(2,4,6-trichlorophenyl).

Table I-5b

Table I-5b is identical to Table I-1, except that R^(x) isC(O)O(4-nitrophenyl).

Table I-6

Table I-6 is identical to Table I-1, except that R^(x) is C(O)OH andR^(y) is C(O)OH.

Table I-7

Table I-7 is identical to Table I-1, except that R^(x) is C(O)OH andR^(y) is C(O)OMe.

Table I-8

Table I-8 is identical to Table I-1, except that R^(x) is C(O)OH andR^(y) is C(O)OEt.

Table I-9

Table I-9 is identical to Table I-1, except that R^(x) is C(O)OH andR^(y) is C(O)OC(CH₃)₃.

Table I-10

Table I-10 is identical to Table I-1, except that R^(x) is C(O)OH andR^(y) is C(O)OPh.

Table I-10a

Table I-10a identical to Table I-1, except that R^(x) is C(O)OH andR^(y) is C(O)O(2,4,6-trichlorophenyl).

Table I-10b

Table I-10b identical to Table I-1, except that R^(x) is C(O)OH andR^(y) is C(O)O(4-nitrophenyl).

Table I-11

Table I-11 is identical to Table I-1, except that R^(x) is C(O)OPh andR^(y) is C(O)OMe.

Table I-12

Table I-12 is identical to Table I-1, except that R^(x) is C(O)OPh andR^(y) is C(O)OEt.

Table I-13

Table I-13 is identical to Table I-1, except that R^(x) is C(O)OPh andR^(y) is C(O)OC(CH₃)₃.

Table I-14

Table I-14 is identical to Table I-1, except that R^(x) is C(O)OPh andR^(y) is C(O)OPh.

Table I-14a

Table I-14a is identical to Table I-1, except that R^(x) is C(O)OPh andR^(y) is C(O)O(2,4,6-trichlorophenyl).

Table I-14b

Table I-14b is identical to Table I-1, except that R^(x) is C(O)OPh andR^(y) is C(O)O(4-nitrophenyl).

Table I-15

Table I-15 is identical to Table I-1, except that R^(x) is C(O)Cl andR^(y) is C(O)Cl.

Table I-16

Table I-16 is identical to Table I-1, except that R^(x) is C(O)OMe andR^(y) is C(O)OMe.

Table I-17

Table I-17 is identical to Table I-1, except that R^(x) is C(O)OEt andR^(y) is C(O)OEt.

Table I-18

Table I-18 is identical to Table I-1, except that R^(x) is C(O)OC(CH₃)₃and R^(y) is C(O)OC(CH₃)₃.

Table I-19

Table I-19 is identical to Table I-1, except that R^(x) isC(O)O(2,4,6-trichlorophenyl) and R^(y) is C(O)O(2,4,6-trichlorophenyl).

Table I-19a

Table I-19a is identical to Table I-1, except that R^(x) isC(O)O(4-nitrophenyl) and R^(y) is C(O)O(4-nitrophenyl).

Table I-20

Table I-20 is identical to Table I-1, except that R^(x) isC(O)(3-methyl-2-pyridinylamino) and R^(y) is C(O)OH.

Table I-21

Table I-21 is identical to Table I-1, except that R^(x) isC(O)(3-methyl-2-pyridinylamino) and R^(y) is C(O)OMe.

Table I-22

Table I-22 is identical to Table I-1, except that R^(x) isC(O)(3-methyl-2-pyridinylamino) and R^(y) is C(O)OEt.

Table I-23

Table I-23 is identical to Table I-1, except that R^(x) isC(O)(3-methyl-2-pyridinylamino) and R^(y) is C(O)OPh.

Table I-23a

Table I-23a is identical to Table I-1, except that R^(x) isC(O)(3-methyl-2-pyridinylamino) and R^(y) isC(O)O(2,4,6-trichlorophenyl).

Table I-23b

Table I-23b is identical to Table I-1, except that R^(x) isC(O)(3-methyl-2-pyridinylamino) and R^(y) is C(O)O(4-nitrophenyl).

Table I-24

Table I-24 is identical to Table I-1, except that R^(x) isC(O)(3-methyl-2-pyridinylamino) and R^(y) is C(O)OC(CH₃)₃.

Table I-24a

Table I-24a is identical to Table I-1, except that the chemicalstructure under the Table I-24a heading is replaced with the followingstructure, and R is Cl. The groups R^(x) and R^(y) found in Table I-1are not relevant to Table I-24a, as the CH(R^(x))(R^(y)) moiety in thestructure of Table I-1 is replaced with a R group in the structure ofTable I-24a.

For example, the first compound in Table I-24a is the structure shownimmediately above wherein R^(a), R^(b), R^(c), R^(d) and R^(e) are H,and R is Cl.

Table I-24b

Table I-24b is identical to Table I-24a, except that R is Br.

Table I-24c

Table I-24c is identical to Table I-24a, except that R is I.

Table I-24d

Table I-24d is identical to Table I-24a, except that R is CH₂OH.

Table I-24e

Table I-24e is identical to Table I-24a, except that R is CH₂CN.

Table I-24f

Table I-24f is identical to Table I-24a, except that R is CH₂Cl.

Table I-24g

Table I-24g is identical to Table I-24a, except that R is CH(CN)CO₂Me.

Table I-24h

Table I-24h is identical to Table I-24a, except that R is CH(CN)CO₂Et.

TABLE I-25

R^(x) R^(y) R is CF₃ H C(O)O(2,4,6-trichlorophenyl) HC(O)O(4-nitrophenyl) C(O)OH C(O)O(4-nitrophenyl) C(O)OHC(O)O(2,4,6-trichlorophenyl) C(O)OH C(O)(3-methyl-2-pyridinylamino)C(O)OMe C(O)(3-methyl-2-pyridinylamino) C(O)OEtC(O)(3-methyl-2-pyridinylamino) C(O)OPh C(O)O(4-nitrophenyl) C(O)OPhC(O)O(2,4,6-trichlorophenyl) C(O)OPh C(O)(3-methyl-2-pyridinylamino)C(O)OC(CH₃)₃ C(O)OPh C(O)OC(CH₃)₃ C(O)(3-methyl-2-pyridinylamino)C(O)O(4-nitrophenyl) C(O)O(4-nitrophenyl) C(O)O(4-nitrophenyl)C(O)(3-methyl-2-pyridinylamino) C(O)O(2,4,6-trichlorophenyl)C(O)O(2,4,6-trichlorophenyl) C(O)O(2,4,6-trichlorophenyl)C(O)(3-methyl-2-pyridinylamino) C(O)OH C(O)OH C(O)OH C(O)OMe C(O)OHC(O)OEt C(O)OH C(O)OPh C(O)OH C(O)OC(CH₃)₃ C(O)Cl C(O)Cl C(O)OMe C(O)OMeC(O)OEt C(O)OEt C(O)OPh C(O)OPh C(O)OC(CH₃)₃ C(O)OC(CH₃)₃ C(O)OMeC(O)OPh C(O)OEt C(O)OPh H C(O)OH H C(O)OMe H C(O)OEt H C(O)OPh HC(O)OC(CH₃)₃ R is H H C(O)O(2,4,6-trichlorophenyl) HC(O)O(4-nitrophenyl) C(O)OH C(O)O(4-nitrophenyl) C(O)OHC(O)O(2,4,6-trichlorophenyl) C(O)OH C(O)(3-methyl-2-pyridinylamino)C(O)OMe C(O)(3-methyl-2-pyridinylamino) C(O)OEtC(O)(3-methyl-2-pyridinylamino) C(O)OPh C(O)O(4-nitrophenyl) C(O)OPhC(O)O(2,4,6-trichlorophenyl) C(O)OPh C(O)(3-methyl-2-pyridinylamino)C(O)OC(CH₃)₃ C(O)OPh C(O)OC(CH₃)₃ C(O)(3-methyl-2-pyridinylamino)C(O)O(4-nitrophenyl) C(O)O(4-nitrophenyl) C(O)O(4-nitrophenyl)C(O)(3-methyl-2-pyridinylamino) C(O)O(2,4,6-trichlorophenyl)C(O)O(2,4,6-trichlorophenyl) C(O)O(2,4,6-trichlorophenyl)C(O)(3-methyl-2-pyridinylamino) C(O)OH C(O)OH C(O)OH C(O)OMe C(O)OHC(O)OEt C(O)OH C(O)OPh C(O)OH C(O)OC(CH₃)₃ C(O)Cl C(O)Cl C(O)OMe C(O)OMeC(O)OEt C(O)OEt C(O)OPh C(O)OPh C(O)OC(CH₃)₃ C(O)OC(CH₃)₃ C(O)OMeC(O)OPh C(O)OEt C(O)OPh H C(O)OH H C(O)OMe H C(O)OEt H C(O)OPh HC(O)OC(CH₃)₃ R is Cl H C(O)O(2,4,6-trichlorophenyl) HC(O)O(4-nitrophenyl) C(O)OH C(O)O(4-nitrophenyl) C(O)OHC(O)O(2,4,6-trichlorophenyl) C(O)OH C(O)(3-methyl-2-pyridinylamino)C(O)OMe C(O)(3-methyl-2-pyridinylamino) C(O)OEtC(O)(3-methyl-2-pyridinylamino) C(O)OPh C(O)O(4-nitrophenyl) C(O)OPhC(O)O(2,4,6-trichlorophenyl) C(O)OPh C(O)(3-methyl-2-pyridinylamino)C(O)OC(CH₃)₃ C(O)OPh C(O)OC(CH₃)₃ C(O)(3-methyl-2-pyridinylamino)C(O)O(4-nitrophenyl) C(O)O(4-nitrophenyl) C(O)O(4-nitrophenyl)C(O)(3-methyl-2-pyridinylamino) C(O)O(2,4,6-trichlorophenyl)C(O)O(2,4,6-trichlorophenyl) C(O)O(2,4,6-trichlorophenyl)C(O)(3-methyl-2-pyridinylamino) C(O)OH C(O)OH C(O)OH C(O)OMe C(O)OHC(O)OEt C(O)OH C(O)OPh C(O)OH C(O)OC(CH₃)₃ C(O)Cl C(O)C₁ C(O)OMe C(O)OMeC(O)OEt C(O)OEt C(O)OPh C(O)OPh C(O)OC(CH₃)₃ C(O)OC(CH₃)₃ C(O)OMeC(O)OPh C(O)OEt C(O)OPh H C(O)OH H C(O)OMe H C(O)OEt H C(O)OPh HC(O)OC(CH₃)₃ R is Br H C(O)O(2,4,6-trichlorophenyl) HC(O)O(4-nitrophenyl) C(O)OH C(O)O(4-nitrophenyl) C(O)OHC(O)O(2,4,6-trichlorophenyl) C(O)OH C(O)(3-methyl-2-pyridinylamino)C(O)OMe C(O)(3-methyl-2-pyridinylamino) C(O)OEtC(O)(3-methyl-2-pyridinylamino) C(O)OPh C(O)O(4-nitrophenyl) C(O)OPhC(O)O(2,4,6-trichlorophenyl) C(O)OPh C(O)(3-methyl-2-pyridinylamino)C(O)OC(CH₃)₃ C(O)OPh C(O)OC(CH₃)₃ C(O)(3-methyl-2-pyridinylamino)C(O)O(4-nitrophenyl) C(O)O(4-nitrophenyl) C(O)O(4-nitrophenyl)C(O)(3-methyl-2-pyridinylamino) C(O)O(2,4,6-trichlorophenyl)C(O)O(2,4,6-trichlorophenyl) C(O)O(2,4,6-trichlorophenyl)C(O)(3-methyl-2-pyridinylamino) C(O)OH C(O)OH C(O)OH C(O)OMe C(O)OHC(O)OEt C(O)OH C(O)OPh C(O)OH C(O)OC(CH₃)₃ C(O)Cl C(O)Cl C(O)OMe C(O)OMeC(O)OEt C(O)OEt C(O)OPh C(O)OPh C(O)OC(CH₃)₃ C(O)OC(CH₃)₃ C(O)OMeC(O)OPh C(O)OEt C(O)OPh H C(O)OH H C(O)OMe H C(O)OEt H C(O)OPh HC(O)OC(CH₃)₃ R is I H C(O)O(2,4,6-trichlorophenyl) HC(O)O(4-nitrophenyl) C(O)OH C(O)O(4-nitrophenyl) C(O)OHC(O)O(2,4,6-trichlorophenyl) C(O)OH C(O)(3-methyl-2-pyridinylamino)C(O)OMe C(O)(3-methyl-2-pyridinylamino) C(O)OEtC(O)(3-methyl-2-pyridinylamino) C(O)OPh C(O)O(4-nitrophenyl) C(O)OPhC(O)O(2,4,6-trichlorophenyl) C(O)OPh C(O)(3-methyl-2-pyridinylamino)C(O)OC(CH₃)₃ C(O)OPh C(O)OC(CH₃)₃ C(O)(3-methyl-2-pyridinylamino)C(O)O(4-nitrophenyl) C(O)O(4-nitrophenyl) C(O)O(4-nitrophenyl)C(O)(3-methyl-2-pyridinylamino) C(O)O(2,4,6-trichlorophenyl)C(O)O(2,4,6-trichlorophenyl) C(O)O(2,4,6-trichlorophenyl)C(O)(3-methyl-2-pyridinylamino) C(O)OH C(O)OH C(O)OH C(O)OMe C(O)OHC(O)OEt C(O)OH C(O)OPh C(O)OH C(O)OC(CH₃)₃ C(O)Cl C(O)Cl C(O)OMe C(O)OMeC(O)OEt C(O)OEt C(O)OPh C(O)OPh C(O)OC(CH₃)₃ C(O)OC(CH₃)₃ C(O)OMeC(O)OPh C(O)OEt C(O)OPh H C(O)OH H C(O)OMe H C(O)OEt H C(O)OPh HC(O)OC(CH₃)₃ R is NH₂ H C(O)O(2,4,6-trichlorophenyl) HC(O)O(4-nitrophenyl) C(O)OH C(O)O(4-nitrophenyl) C(O)OHC(O)O(2,4,6-trichlorophenyl) C(O)OH C(O)(3-methyl-2-pyridinylamino)C(O)OMe C(O)(3-methyl-2-pyridinylamino) C(O)OEtC(O)(3-methyl-2-pyridinylamino) C(O)OPh C(O)O(4-nitrophenyl) C(O)OPhC(O)O(2,4,6-trichlorophenyl) C(O)OPh C(O)(3-methyl-2-pyridinylamino)C(O)OC(CH₃)₃ C(O)OPh C(O)OC(CH₃)₃ C(O)(3-methyl-2-pyridinylamino)C(O)O(4-nitrophenyl) C(O)O(4-nitrophenyl) C(O)O(4-nitrophenyl)C(O)(3-methyl-2-pyridinylamino) C(O)O(2,4,6-trichlorophenyl)C(O)O(2,4,6-trichlorophenyl) C(O)O(2,4,6-trichlorophenyl)C(O)(3-methyl-2-pyridinylamino) C(O)OH C(O)OH C(O)OH C(O)OMe C(O)OHC(O)OEt C(O)OH C(O)OPh C(O)OH C(O)OC(CH₃)₃ C(O)Cl C(O)Cl C(O)OMe C(O)OMeC(O)OEt C(O)OEt C(O)OPh C(O)OPh C(O)OC(CH₃)₃ C(O)OC(CH₃)₃ C(O)OMeC(O)OPh C(O)OEt C(O)OPh H C(O)OH H C(O)OMe H C(O)OEt H C(O)OPh HC(O)OC(CH₃)₃ R is 2-chloro-4-(trifluoromethyl)phenyl HC(O)O(2,4,6-trichlorophenyl) H C(O)O(4-nitrophenyl) C(O)OHC(O)O(4-nitrophenyl) C(O)OH C(O)O(2,4,6-trichlorophenyl) C(O)OHC(O)(3-methyl-2-pyridinylamino) C(O)OMe C(O)(3-methyl-2-pyridinylamino)C(O)OEt C(O)(3-methyl-2-pyridinylamino) C(O)OPh C(O)O(4-nitrophenyl)C(O)OPh C(O)O(2,4,6-trichlorophenyl) C(O)OPhC(O)(3-methyl-2-pyridinylamino) C(O)OC(CH₃)₃ C(O)OPh C(O)OC(CH₃)₃C(O)(3-methyl-2-pyridinylamino) C(O)O(4-nitrophenyl)C(O)O(4-nitrophenyl) C(O)O(4-nitrophenyl)C(O)(3-methyl-2-pyridinylamino) C(O)O(2,4,6-trichlorophenyl)C(O)O(2,4,6-trichlorophenyl) C(O)O(2,4,6-trichlorophenyl)C(O)(3-methyl-2-pyridinylamino) C(O)OH C(O)OH C(O)OH C(O)OMe C(O)OHC(O)OEt C(O)OH C(O)OPh C(O)OH C(O)OC(CH₃)₃ C(O)Cl C(O)Cl C(O)OMe C(O)OMeC(O)OEt C(O)OEt C(O)OPh C(O)OPh C(O)OC(CH₃)₃ C(O)OC(CH₃)₃ C(O)OMeC(O)OPh C(O)OEt C(O)OPh H C(O)OH H C(O)OMe H C(O)OEt H C(O)OPh HC(O)OC(CH₃)₃ R is 2-fluoro-5-(trifluoromethyl)phenyl HC(O)O(2,4,6-trichlorophenyl) H C(O)O(4-nitrophenyl) C(O)OHC(O)O(4-nitrophenyl) C(O)OH C(O)O(2,4,6-trichlorophenyl) C(O)OHC(O)(3-methyl-2-pyridinylamino) C(O)OMe C(O)(3-methyl-2-pyridinylamino)C(O)OEt C(O)(3-methyl-2-pyridinylamino) C(O)OPh C(O)O(4-nitrophenyl)C(O)OPh C(O)O(2,4,6-trichlorophenyl) C(O)OPhC(O)(3-methyl-2-pyridinylamino) C(O)OC(CH₃)₃ C(O)OPh C(O)OC(CH₃)₃C(O)(3-methyl-2-pyridinylamino) C(O)O(4-nitrophenyl)C(O)O(4-nitrophenyl) C(O)O(4-nitrophenyl)C(O)(3-methyl-2-pyridinylamino) C(O)O(2,4,6-trichlorophenyl)C(O)O(2,4,6-trichlorophenyl) C(O)O(2,4,6-trichlorophenyl)C(O)(3-methyl-2-pyridinylamino) C(O)OH C(O)OH C(O)OH C(O)OMe C(O)OHC(O)OEt C(O)OH C(O)OPh C(O)OH C(O)OC(CH₃)₃ C(O)Cl C(O)Cl C(O)OMe C(O)OMeC(O)OEt C(O)OEt C(O)OPh C(O)OPh C(O)OC(CH₃)₃ C(O)OC(CH₃)₃ C(O)OMeC(O)OPh C(O)OEt C(O)OPh H C(O)OH H C(O)OMe H C(O)OEt H C(O)OPh HC(O)OC(CH₃)₃ R is 2-chloro-4-cyanophenyl H C(O)O(2,4,6-trichlorophenyl)H C(O)O(4-nitrophenyl) C(O)OH C(O)O(4-nitrophenyl) C(O)OHC(O)O(2,4,6-trichlorophenyl) C(O)OH C(O)(3-methyl-2-pyridinylamino)C(O)OMe C(O)(3-methyl-2-pyridinylamino) C(O)OEtC(O)(3-methyl-2-pyridinylamino) C(O)OPh C(O)O(4-nitrophenyl) C(O)OPhC(O)O(2,4,6-trichlorophenyl) C(O)OPh C(O)(3-methyl-2-pyridinylamino)C(O)OC(CH₃)₃ C(O)OPh C(O)OC(CH₃)₃ C(O)(3-methyl-2-pyridinylamino)C(O)O(4-nitrophenyl) C(O)O(4-nitrophenyl) C(O)O(4-nitrophenyl)C(O)(3-methyl-2-pyridinylamino) C(O)O(2,4,6-trichlorophenyl)C(O)O(2,4,6-trichlorophenyl) C(O)O(2,4,6-trichlorophenyl)C(O)(3-methyl-2-pyridinylamino) C(O)OH C(O)OH C(O)OH C(O)OMe C(O)OHC(O)OEt C(O)OH C(O)OPh C(O)OH C(O)OC(CH₃)₃ C(O)Cl C(O)Cl C(O)OMe C(O)OMeC(O)OEt C(O)OEt C(O)OPh C(O)OPh C(O)OC(CH₃)₃ C(O)OC(CH₃)₃ C(O)OMeC(O)OPh C(O)OEt C(O)OPh H C(O)OH H C(O)OMe H C(O)OEt H C(O)OPh HC(O)OC(CH₃)₃ R is 2-fluoro-4-cyanophenyl H C(O)O(2,4,6-trichlorophenyl)H C(O)O(4-nitrophenyl) C(O)OH C(O)O(4-nitrophenyl) C(O)OHC(O)O(2,4,6-trichlorophenyl) C(O)OH C(O)(3-methyl-2-pyridinylamino)C(O)OMe C(O)(3-methyl-2-pyridinylamino) C(O)OEtC(O)(3-methyl-2-pyridinylamino) C(O)OPh C(O)O(4-nitrophenyl) C(O)OPhC(O)O(2,4,6-trichlorophenyl) C(O)OPh C(O)(3-methyl-2-pyridinylamino)C(O)OC(CH₃)₃ C(O)OPh C(O)OC(CH₃)₃ C(O)(3-methyl-2-pyridinylamino)C(O)O(4-nitrophenyl) C(O)O(4-nitrophenyl) C(O)O(4-nitrophenyl)C(O)(3-methyl-2-pyridinylamino) C(O)O(2,4,6-trichlorophenyl)C(O)O(2,4,6-trichlorophenyl) C(O)O(2,4,6-trichlorophenyl)C(O)(3-methyl-2-pyridinylamino) C(O)OH C(O)OH C(O)OH C(O)OMe C(O)OHC(O)OEt C(O)OH C(O)OPh C(O)OH C(O)OC(CH₃)₃ C(O)Cl C(O)Cl C(O)OMe C(O)OMeC(O)OEt C(O)OEt C(O)OPh C(O)OPh C(O)OC(CH₃)₃ C(O)OC(CH₃)₃ C(O)OMeC(O)OPh C(O)OEt C(O)OPh H C(O)OH H C(O)OMe H C(O)OEt H C(O)OPh HC(O)OC(CH₃)₃

TABLE I-26

R^(x) R^(y) R is H H C(O)O(2,4,6-trichlorophenyl) H C(O)O(4-nitrophenyl)C(O)OH C(O)O(4-nitrophenyl) C(O)OH C(O)O(2,4,6-trichlorophenyl) C(O)OHC(O)(3-methyl-2-pyridinylamino) C(O)OMe C(O)(3-methyl-2-pyridinylamino)C(O)OEt C(O)(3-methyl-2-pyridinylamino) C(O)OPh C(O)O(4-nitrophenyl)C(O)OPh C(O)O(2,4,6-trichlorophenyl) C(O)OPhC(O)(3-methyl-2-pyridinylamino) C(O)OC(CH₃)₃ C(O)OPh C(O)OC(CH₃)₃C(O)(3-methyl-2-pyridinylamino) C(O)O(4-nitrophenyl)C(O)O(4-nitrophenyl) C(O)O(4-nitrophenyl)C(O)(3-methyl-2-pyridinylamino) C(O)O(2,4,6-trichlorophenyl)C(O)O(2,4,6-trichlorophenyl) C(O)O(2,4,6-trichlorophenyl)C(O)(3-methyl-2-pyridinylamino) C(O)OH C(O)OH C(O)OH C(O)OMe C(O)OHC(O)OEt C(O)OH C(O)OPh C(O)OH C(O)OC(CH₃)₃ C(O)Cl C(O)Cl C(O)OMe C(O)OMeC(O)OEt C(O)OEt C(O)OPh C(O)OPh C(O)OC(CH₃)₃ C(O)OC(CH₃)₃ C(O)OMeC(O)OPh C(O)OEt C(O)OPh H C(O)OH H C(O)OMe H C(O)OEt H C(O)OPh HC(O)OC(CH₃)₃ R is CF₃ H C(O)O(2,4,6-trichlorophenyl) HC(O)O(4-nitrophenyl) C(O)OH C(O)O(4-nitrophenyl) C(O)OHC(O)O(2,4,6-trichlorophenyl) C(O)OH C(O)(3-methyl-2-pyridinylamino)C(O)OMe C(O)(3-methyl-2-pyridinylamino) C(O)OEtC(O)(3-methyl-2-pyridinylamino) C(O)OPh C(O)O(4-nitrophenyl) C(O)OPhC(O)O(2,4,6-trichlorophenyl) C(O)OPh C(O)(3-methyl-2-pyridinylamino)C(O)OC(CH₃)₃ C(O)OPh C(O)OC(CH₃)₃ C(O)(3-methyl-2-pyridinylamino)C(O)O(4-nitrophenyl) C(O)O(4-nitrophenyl) C(O)O(4-nitrophenyl)C(O)(3-methyl-2-pyridinylamino) C(O)O(2,4,6-trichlorophenyl)C(O)O(2,4,6-trichlorophenyl) C(O)O(2,4,6-trichlorophenyl)C(O)(3-methyl-2-pyridinylamino) C(O)OH C(O)OH C(O)OH C(O)OMe C(O)OHC(O)OEt C(O)OH C(O)OPh C(O)OH C(O)OC(CH₃)₃ C(O)Cl C(O)Cl C(O)OMe C(O)OMeC(O)OEt C(O)OEt C(O)OPh C(O)OPh C(O)OC(CH₃)₃ C(O)OC(CH₃)₃ C(O)OMeC(O)OPh C(O)OEt C(O)OPh H C(O)OH H C(O)OMe H C(O)OEt H C(O)OPh HC(O)OC(CH₃)₃ R is F H C(O)O(2,4,6-trichlorophenyl) HC(O)O(4-nitrophenyl) C(O)OH C(O)O(4-nitrophenyl) C(O)OHC(O)O(2,4,6-trichlorophenyl) C(O)OH C(O)(3-methyl-2-pyridinylamino)C(O)OMe C(O)(3-methyl-2-pyridinylamino) C(O)OEtC(O)(3-methyl-2-pyridinylamino) C(O)OPh C(O)O(4-nitrophenyl) C(O)OPhC(O)O(2,4,6-trichlorophenyl) C(O)OPh C(O)(3-methyl-2-pyridinylamino)C(O)OC(CH₃)₃ C(O)OPh C(O)OC(CH₃)₃ C(O)(3-methyl-2-pyridinylamino)C(O)O(4-nitrophenyl) C(O)O(4-nitrophenyl) C(O)O(4-nitrophenyl)C(O)(3-methyl-2-pyridinylamino) C(O)O(2,4,6-trichlorophenyl)C(O)O(2,4,6-trichlorophenyl) C(O)O(2,4,6-trichlorophenyl)C(O)(3-methyl-2-pyridinylamino) C(O)OH C(O)OH C(O)OH C(O)OMe C(O)OHC(O)OEt C(O)OH C(O)OPh C(O)OH C(O)OC(CH₃)₃ C(O)Cl C(O)Cl C(O)OMe C(O)OMeC(O)OEt C(O)OEt C(O)OPh C(O)OPh C(O)OC(CH₃)₃ C(O)OC(CH₃)₃ C(O)OMeC(O)OPh C(O)OEt C(O)OPh H C(O)OH H C(O)OMe H C(O)OEt H C(O)OPh HC(O)OC(CH₃)₃ R is Cl H C(O)O(2,4,6-trichlorophenyl) HC(O)O(4-nitrophenyl) C(O)OH C(O)O(4-nitrophenyl) C(O)OHC(O)O(2,4,6-trichlorophenyl) C(O)OH C(O)(3-methyl-2-pyridinylamino)C(O)OMe C(O)(3-methyl-2-pyridinylamino) C(O)OEtC(O)(3-methyl-2-pyridinylamino) C(O)OPh C(O)O(4-nitrophenyl) C(O)OPhC(O)O(2,4,6-trichlorophenyl) C(O)OPh C(O)(3-methyl-2-pyridinylamino)C(O)OC(CH₃)₃ C(O)OPh C(O)OC(CH₃)₃ C(O)(3-methyl-2-pyridinylamino)C(O)O(4-nitrophenyl) C(O)O(4-nitrophenyl) C(O)O(4-nitrophenyl)C(O)(3-methyl-2-pyridinylamino) C(O)O(2,4,6-trichlorophenyl)C(O)O(2,4,6-trichlorophenyl) C(O)O(2,4,6-trichlorophenyl)C(O)(3-methyl-2-pyridinylamino) C(O)OH C(O)OH C(O)OH C(O)OMe C(O)OHC(O)OEt C(O)OH C(O)OPh C(O)OH C(O)OC(CH₃)₃ C(O)Cl C(O)Cl C(O)OMe C(O)OMeC(O)OEt C(O)OEt C(O)OPh C(O)OPh C(O)OC(CH₃)₃ C(O)OC(CH₃)₃ C(O)OMeC(O)OPh C(O)OEt C(O)OPh H C(O)OH H C(O)OMe H C(O)OEt H C(O)OPh HC(O)OC(CH₃)₃ R is Br H C(O)O(2,4,6-trichlorophenyl) HC(O)O(4-nitrophenyl) C(O)OH C(O)O(4-nitrophenyl) C(O)OHC(O)O(2,4,6-trichlorophenyl) C(O)OH C(O)(3-methyl-2-pyridinylamino)C(O)OMe C(O)(3-methyl-2-pyridinylamino) C(O)OEtC(O)(3-methyl-2-pyridinylamino) C(O)OPh C(O)O(4-nitrophenyl) C(O)OPhC(O)O(2,4,6-trichlorophenyl) C(O)OPh C(O)(3-methyl-2-pyridinylamino)C(O)OC(CH₃)₃ C(O)OPh C(O)OC(CH₃)₃ C(O)(3-methyl-2-pyridinylamino)C(O)O(4-nitrophenyl) C(O)O(4-nitrophenyl) C(O)O(4-nitrophenyl)C(O)(3-methyl-2-pyridinylamino) C(O)O(2,4,6-trichlorophenyl)C(O)O(2,4,6-trichlorophenyl) C(O)O(2,4,6-trichlorophenyl)C(O)(3-methyl-2-pyridinylamino) C(O)OH C(O)OH C(O)OH C(O)OMe C(O)OHC(O)OEt C(O)OH C(O)OPh C(O)OH C(O)OC(CH₃)₃ C(O)Cl C(O)Cl C(O)OMe C(O)OMeC(O)OEt C(O)OEt C(O)OPh C(O)OPh C(O)OC(CH₃)₃ C(O)OC(CH₃)₃ C(O)OMeC(O)OPh C(O)OEt C(O)OPh H C(O)OH H C(O)OMe H C(O)OEt H C(O)OPh HC(O)OC(CH₃)₃ R is I H C(O)O(2,4,6-trichlorophenyl) HC(O)O(4-nitrophenyl) C(O)OH C(O)O(4-nitrophenyl) C(O)OHC(O)O(2,4,6-trichlorophenyl) C(O)OH C(O)(3-methyl-2-pyridinylamino)C(O)OMe C(O)(3-methyl-2-pyridinylamino) C(O)OEtC(O)(3-methyl-2-pyridinylamino) C(O)OPh C(O)O(4-nitrophenyl) C(O)OPhC(O)O(2,4,6-trichlorophenyl) C(O)OPh C(O)(3-methyl-2-pyridinylamino)C(O)OC(CH₃)₃ C(O)OPh C(O)OC(CH₃)₃ C(O)(3-methyl-2-pyridinylamino)C(O)O(4-nitrophenyl) C(O)O(4-nitrophenyl) C(O)O(4-nitrophenyl)C(O)(3-methyl-2-pyridinylamino) C(O)O(2,4,6-trichlorophenyl)C(O)O(2,4,6-trichlorophenyl) C(O)O(2,4,6-trichlorophenyl)C(O)(3-methyl-2-pyridinylamino) C(O)OH C(O)OH C(O)OH C(O)OMe C(O)OHC(O)OEt C(O)OH C(O)OPh C(O)OH C(O)OC(CH₃)₃ C(O)Cl C(O)Cl C(O)OMe C(O)OMeC(O)OEt C(O)OEt C(O)OPh C(O)OPh C(O)OC(CH₃)₃ C(O)OC(CH₃)₃ C(O)OMeC(O)OPh C(O)OEt C(O)OPh H C(O)OH H C(O)OMe H C(O)OEt H C(O)OPh HC(O)OC(CH₃)₃ R is NH₂ H C(O)O(2,4,6-trichlorophenyl) HC(O)O(4-nitrophenyl) C(O)OH C(O)O(4-nitrophenyl) C(O)OHC(O)O(2,4,6-trichlorophenyl) C(O)OH C(O)(3-methyl-2-pyridinylamino)C(O)OMe C(O)(3-methyl-2-pyridinylamino) C(O)OEtC(O)(3-methyl-2-pyridinylamino) C(O)OPh C(O)O(4-nitrophenyl) C(O)OPhC(O)O(2,4,6-trichlorophenyl) C(O)OPh C(O)(3-methyl-2-pyridinylamino)C(O)OC(CH₃)₃ C(O)OPh C(O)OC(CH₃)₃ C(O)(3-methyl-2-pyridinylamino)C(O)O(4-nitrophenyl) C(O)O(4-nitrophenyl) C(O)O(4-nitrophenyl)C(O)(3-methyl-2-pyridinylamino) C(O)O(2,4,6-trichlorophenyl)C(O)O(2,4,6-trichlorophenyl) C(O)O(2,4,6-trichlorophenyl)C(O)(3-methyl-2-pyridinylamino) C(O)OH C(O)OH C(O)OH C(O)OMe C(O)OHC(O)OEt C(O)OH C(O)OPh C(O)OH C(O)OC(CH₃)₃ C(O)Cl C(O)Cl C(O)OMe C(O)OMeC(O)OEt C(O)OEt C(O)OPh C(O)OPh C(O)OC(CH₃)₃ C(O)OC(CH₃)₃ C(O)OMeC(O)OPh C(O)OEt C(O)OPh H C(O)OH H C(O)OMe H C(O)OEt H C(O)OPh HC(O)OC(CH₃)₃ R is 2-chloro-4-(trifluoromethyl)phenyl HC(O)O(2,4,6-trichlorophenyl) H C(O)O(4-nitrophenyl) C(O)OHC(O)O(4-nitrophenyl) C(O)OH C(O)O(2,4,6-trichlorophenyl) C(O)OHC(O)(3-methyl-2-pyridinylamino) C(O)OMe C(O)(3-methyl-2-pyridinylamino)C(O)OEt C(O)(3-methyl-2-pyridinylamino) C(O)OPh C(O)O(4-nitrophenyl)C(O)OPh C(O)O(2,4,6-trichlorophenyl) C(O)OPhC(O)(3-methyl-2-pyridinylamino) C(O)OC(CH₃)₃ C(O)OPh C(O)OC(CH₃)₃C(O)(3-methyl-2-pyridinylamino) C(O)O(4-nitrophenyl)C(O)O(4-nitrophenyl) C(O)O(4-nitrophenyl)C(O)(3-methyl-2-pyridinylamino) C(O)O(2,4,6-trichlorophenyl)C(O)O(2,4,6-trichlorophenyl) C(O)O(2,4,6-trichlorophenyl)C(O)(3-methyl-2-pyridinylamino) C(O)OH C(O)OH C(O)OH C(O)OMe C(O)OHC(O)OEt C(O)OH C(O)OPh C(O)OH C(O)OC(CH₃)₃ C(O)Cl C(O)Cl C(O)OMe C(O)OMeC(O)OEt C(O)OEt C(O)OPh C(O)OPh C(O)OC(CH₃)₃ C(O)OC(CH₃)₃ C(O)OMeC(O)OPh C(O)OEt C(O)OPh H C(O)OH H C(O)OMe H C(O)OEt H C(O)OPh HC(O)OC(CH₃)₃ R is 2-fluoro-5-(trifluoromethyl)phenyl HC(O)O(2,4,6-trichlorophenyl) H C(O)O(4-nitrophenyl) C(O)OHC(O)O(4-nitrophenyl) C(O)OH C(O)O(2,4,6-trichlorophenyl) C(O)OHC(O)(3-methyl-2-pyridinylamino) C(O)OMe C(O)(3-methyl-2-pyridinylamino)C(O)OEt C(O)(3-methyl-2-pyridinylamino) C(O)OPh C(O)O(4-nitrophenyl)C(O)OPh C(O)O(2,4,6-trichlorophenyl) C(O)OPhC(O)(3-methyl-2-pyridinylamino) C(O)OC(CH₃)₃ C(O)OPh C(O)OC(CH₃)₃C(O)(3-methyl-2-pyridinylamino) C(O)O(4-nitrophenyl)C(O)O(4-nitrophenyl) C(O)O(4-nitrophenyl)C(O)(3-methyl-2-pyridinylamino) C(O)O(2,4,6-trichlorophenyl)C(O)O(2,4,6-trichlorophenyl) C(O)O(2,4,6-trichlorophenyl)C(O)(3-methyl-2-pyridinylamino) C(O)OH C(O)OH C(O)OH C(O)OMe C(O)OHC(O)OEt C(O)OH C(O)OPh C(O)OH C(O)OC(CH₃)₃ C(O)Cl C(O)Cl C(O)OMe C(O)OMeC(O)OEt C(O)OEt C(O)OPh C(O)OPh C(O)OC(CH₃)₃ C(O)OC(CH₃)₃ C(O)OMeC(O)OPh C(O)OEt C(O)OPh H C(O)OH H C(O)OMe H C(O)OEt H C(O)OPh HC(O)OC(CH₃)₃ R is 2-chloro-4-cyanophenyl H C(O)O(2,4,6-trichlorophenyl)H C(O)O(4-nitrophenyl) C(O)OH C(O)O(4-nitrophenyl) C(O)OHC(O)O(2,4,6-trichlorophenyl) C(O)OH C(O)(3-methyl-2-pyridinylamino)C(O)OMe C(O)(3-methyl-2-pyridinylamino) C(O)OEtC(O)(3-methyl-2-pyridinylamino) C(O)OPh C(O)O(4-nitrophenyl) C(O)OPhC(O)O(2,4,6-trichlorophenyl) C(O)OPh C(O)(3-methyl-2-pyridinylamino)C(O)OC(CH₃)₃ C(O)OPh C(O)OC(CH₃)₃ C(O)(3-methyl-2-pyridinylamino)C(O)O(4-nitrophenyl) C(O)O(4-nitrophenyl) C(O)O(4-nitrophenyl)C(O)(3-methyl-2-pyridinylamino) C(O)O(2,4,6-trichlorophenyl)C(O)O(2,4,6-trichlorophenyl) C(O)O(2,4,6-trichlorophenyl)C(O)(3-methyl-2-pyridinylamino) C(O)OH C(O)OH C(O)OH C(O)OMe C(O)OHC(O)OEt C(O)OH C(O)OPh C(O)OH C(O)OC(CH₃)₃ C(O)Cl C(O)Cl C(O)OMe C(O)OMeC(O)OEt C(O)OEt C(O)OPh C(O)OPh C(O)OC(CH₃)₃ C(O)OC(CH₃)₃ C(O)OMeC(O)OPh C(O)OEt C(O)OPh H C(O)OH H C(O)OMe H C(O)OEt H C(O)OPh HC(O)OC(CH₃)₃ R is 2-fluoro-4-cyanophenyl H C(O)O(2,4,6-trichlorophenyl)H C(O)O(4-nitrophenyl) C(O)OH C(O)O(4-nitrophenyl) C(O)OHC(O)O(2,4,6-trichlorophenyl) C(O)OH C(O)(3-methyl-2-pyridinylamino)C(O)OMe C(O)(3-methyl-2-pyridinylamino) C(O)OEtC(O)(3-methyl-2-pyridinylamino) C(O)OPh C(O)O(4-nitrophenyl) C(O)OPhC(O)O(2,4,6-trichlorophenyl) C(O)OPh C(O)(3-methyl-2-pyridinylamino)C(O)OC(CH₃)₃ C(O)OPh C(O)OC(CH₃)₃ C(O)(3-methyl-2-pyridinylamino)C(O)O(4-nitrophenyl) C(O)O(4-nitrophenyl) C(O)O(4-nitrophenyl)C(O)(3-methyl-2-pyridinylamino) C(O)O(2,4,6-trichlorophenyl)C(O)O(2,4,6-trichlorophenyl) C(O)O(2,4,6-trichlorophenyl)C(O)(3-methyl-2-pyridinylamino) C(O)OH C(O)OH C(O)OH C(O)OMe C(O)OHC(O)OEt C(O)OH C(O)OPh C(O)OH C(O)OC(CH₃)₃ C(O)Cl C(O)Cl C(O)OMe C(O)OMeC(O)OEt C(O)OEt C(O)OPh C(O)OPh C(O)OC(CH₃)₃ C(O)OC(CH₃)₃ C(O)OMeC(O)OPh C(O)OEt C(O)OPh H C(O)OH H C(O)OMe H C(O)OEt H C(O)OPh HC(O)OC(CH₃)₃

TABLE I-27

R^(x) R^(y) H CF₃ Me CF₃ H Et Me Et H 3-pyridinyl Me 3-pyridinyl H6-fluoro-3-pyridinyl Me 6-fluoro-3-pyridinyl H 6-bromo-3-pyridinyl Me6-bromo-3-pyridinyl H 2-methyl-5-thiazolyl Me 2-methyl-5-thiazolyl HCH₂CHFCF₂Cl Me CH₂CHFCF₂Cl H cyclopropyl Me cyclopropyl H6-methyl-3-pyridinyl Me 6-methyl-3-pyridinyl H 6-chloro-3-pyridinyl Me6-chloro-3-pyridinyl H 5-thiazolyl Me 5-thiazolyl H 2-fluoro-5-thiazolylMe 2-fluoro-5-thiazolyl H 2-chloro-5-thiazolyl Me 2-chloro-5-thiazolyl H1-methyl-4-pyrazolyl Me 1-methyl-4-pyrazolyl H 5-pyrimidinyl Me5-pyrimidinyl H 2-bromo-5-thiazolyl Me 2-bromo-5-thiazolyl H3-methyl-5-isoxazolyl Me 3-methyl-5-isoxazolyl H 2-methyl-5-pyrimidinylMe 2-methyl-5-pyrimidinyl

TABLE I-27a

R^(x) R^(y) H CF₃ Me CF₃ H Et Me Et H 3-pyridinyl Me 3-pyridinyl H6-fluoro-3-pyridinyl Me 6-fluoro-3-pyridinyl H 6-bromo-3-pyridinyl Me6-bromo-3-pyridinyl H 2-methyl-5-thiazolyl Me 2-methyl-5-thiazolyl HCH₂CHFCF₂Cl Me CH₂CHFCF₂Cl H cyclopropyl Me cyclopropyl H6-methyl-3-pyridinyl Me 6-methyl-3-pyridinyl H 6-chloro-3-pyridinyl Me6-chloro-3-pyridinyl H 5-thiazolyl Me 5-thiazolyl H 2-fluoro-5-thiazolylMe 2-fluoro-5-thiazolyl H 2-chloro-5-thiazolyl Me 2-chloro-5-thiazolyl H1-methyl-4-pyrazolyl Me 1-methyl-4-pyrazolyl H 5-pyrimidinyl Me5-pyrimidinyl H 2-bromo-5-thiazolyl Me 2-bromo-5-thiazolyl H3-methyl-5-isoxazolyl Me 3-methyl-5-isoxazolyl H 2-methyl-5-pyrimidinylMe 2-methyl-5-pyrimidinyl

TABLE I-27b

R^(x) R^(y) H CF₃ Me CF₃ H Et Me Et H 3-pyridinyl Me 3-pyridinyl H6-fluoro-3-pyridinyl Me 6-fluoro-3-pyridinyl H 6-bromo-3-pyridinyl Me6-bromo-3-pyridinyl H 2-methyl-5-thiazolyl Me 2-methyl-5-thiazolyl HCH₂CHFCF₂Cl Me CH₂CHFCF₂Cl H cyclopropyl Me cyclopropyl H6-methyl-3-pyridinyl Me 6-methyl-3-pyridinyl H 6-chloro-3-pyridinyl Me6-chloro-3-pyridinyl H 5-thiazolyl Me 5-thiazolyl H 2-fluoro-5-thiazolylMe 2-fluoro-5-thiazolyl H 2-chloro-5-thiazolyl Me 2-chloro-5-thiazolyl H1-methyl-4-pyrazolyl Me 1-methyl-4-pyrazolyl H 5-pyrimidinyl Me5-pyrimidinyl H 2-bromo-5-thiazolyl Me 2-bromo-5-thiazolyl H3-methyl-5-isoxazolyl Me 3-methyl-5-isoxazolyl H 2-methyl-5-pyrimidinylMe 2-methyl-5-pyrimidinyl

TABLE I-27c

R^(x) R^(y) H CF₃ Me CF₃ H Et Me Et H 3-pyridinyl Me 3-pyridinyl H6-fluoro-3-pyridinyl Me 6-fluoro-3-pyridinyl H 6-bromo-3-pyridinyl Me6-bromo-3-pyridinyl H 2-methyl-5-thiazolyl Me 2-methyl-5-thiazolyl HCH₂CHFCF₂Cl Me CH₂CHFCF₂Cl H cyclopropyl Me cyclopropyl H6-methyl-3-pyridinyl Me 6-methyl-3-pyridinyl H 6-chloro-3-pyridinyl Me6-chloro-3-pyridinyl H 5-thiazolyl Me 5-thiazolyl H 2-fluoro-5-thiazolylMe 2-fluoro-5-thiazolyl H 2-chloro-5-thiazolyl Me 2-chloro-5-thiazolyl H1-methyl-4-pyrazolyl Me 1-methyl-4-pyrazolyl H 5-pyrimidinyl Me5-pyrimidinyl H 2-bromo-5-thiazolyl Me 2-bromo-5-thiazolyl H3-methyl-5-isoxazolyl Me 3-methyl-5-isoxazolyl H 2-methyl-5-pyrimidinylMe 2-methyl-5-pyrimidinyl

TABLE I-27d

R^(x) R^(y) H CF₃ Me CF₃ H Et Me Et H 3-pyridinyl Me 3-pyridinyl H6-fluoro-3-pyridinyl Me 6-fluoro-3-pyridinyl H 6-bromo-3-pyridinyl Me6-bromo-3-pyridinyl H 2-methyl-5-thiazolyl Me 2-methyl-5-thiazolyl HCH₂CHFCF₂Cl Me CH₂CHFCF₂Cl H cyclopropyl Me cyclopropyl H6-methyl-3-pyridinyl Me 6-methyl-3-pyridinyl H 6-chloro-3-pyridinyl Me6-chloro-3-pyridinyl H 5-thiazolyl Me 5-thiazolyl H 2-fluoro-5-thiazolylMe 2-fluoro-5-thiazolyl H 2-chloro-5-thiazolyl Me 2-chloro-5-thiazolyl H1-methyl-4-pyrazolyl Me 1-methyl-4-pyrazolyl H 5-pyrimidinyl Me5-pyrimidinyl H 2-bromo-5-thiazolyl Me 2-bromo-5-thiazolyl H3-methyl-5-isoxazolyl Me 3-methyl-5-isoxazolyl H 2-methyl-5-pyrimidinylMe 2-methyl-5-pyrimidinyl

TABLE I-27e

R^(x) R^(y) H CF₃ Me CF₃ H Et Me Et H 3-pyridinyl Me 3-pyridinyl H6-fluoro-3-pyridinyl Me 6-fluoro-3-pyridinyl H 6-bromo-3-pyridinyl Me6-bromo-3-pyridinyl H 2-methyl-5-thiazolyl Me 2-methyl-5-thiazolyl HCH₂CHFCF₂Cl Me CH₂CHFCF₂Cl H cyclopropyl Me cyclopropyl H6-methyl-3-pyridinyl Me 6-methyl-3-pyridinyl H 6-chloro-3-pyridinyl Me6-chloro-3-pyridinyl H 5-thiazolyl Me 5-thiazolyl H 2-fluoro-5-thiazolylMe 2-fluoro-5-thiazolyl H 2-chloro-5-thiazolyl Me 2-chloro-5-thiazolyl H1-methyl-4-pyrazolyl Me 1-methyl-4-pyrazolyl H 5-pyrimidinyl Me5-pyrimidinyl H 2-bromo-5-thiazolyl Me 2-bromo-5-thiazolyl H3-methyl-5-isoxazolyl Me 3-methyl-5-isoxazolyl H 2-methyl-5-pyrimidinylMe 2-methyl-5-pyrimidinyl

TABLE I-27f

R^(x) R^(y) H CF₃ Me CF₃ H Et Me Et H 3-pyridinyl Me 3-pyridinyl H6-fluoro-3-pyridinyl Me 6-fluoro-3-pyridinyl H 6-bromo-3-pyridinyl Me6-bromo-3-pyridinyl H 2-methyl-5-thiazolyl Me 2-methyl-5-thiazolyl HCH₂CHFCF₂Cl Me CH₂CHFCF₂Cl H cyclopropyl Me cyclopropyl H6-methyl-3-pyridinyl Me 6-methyl-3-pyridinyl H 6-chloro-3-pyridinyl Me6-chloro-3-pyridinyl H 5-thiazolyl Me 5-thiazolyl H 2-fluoro-5-thiazolylMe 2-fluoro-5-thiazolyl H 2-chloro-5-thiazolyl Me 2-chloro-5-thiazolyl H1-methyl-4-pyrazolyl Me 1-methyl-4-pyrazolyl H 5-pyrimidinyl Me5-pyrimidinyl H 2-bromo-5-thiazolyl Me 2-bromo-5-thiazolyl H3-methyl-5-isoxazolyl Me 3-methyl-5-isoxazolyl H 2-methyl-5-pyrimidinylMe 2-methyl-5-pyrimidinyl

TABLE I-27g

R^(x) R^(y) H CF₃ Me CF₃ H Et Me Et H 3-pyridinyl Me 3-pyridinyl H6-fluoro-3-pyridinyl Me 6-fluoro-3-pyridinyl H 6-bromo-3-pyridinyl Me6-bromo-3-pyridinyl H 2-methyl-5-thiazolyl Me 2-methyl-5-thiazolyl HCH₂CHFCF₂Cl Me CH₂CHFCF₂Cl H cyclopropyl Me cyclopropyl H6-methyl-3-pyridinyl Me 6-methyl-3-pyridinyl H 6-chloro-3-pyridinyl Me6-chloro-3-pyridinyl H 5-thiazolyl Me 5-thiazolyl H 2-fluoro-5-thiazolylMe 2-fluoro-5-thiazolyl H 2-chloro-5-thiazolyl Me 2-chloro-5-thiazolyl H1-methyl-4-pyrazolyl Me 1-methyl-4-pyrazolyl H 5-pyrimidinyl Me5-pyrimidinyl H 2-bromo-5-thiazolyl Me 2-bromo-5-thiazolyl H3-methyl-5-isoxazolyl Me 3-methyl-5-isoxazolyl H 2-methyl-5-pyrimidinylMe 2-methyl-5-pyrimidinyl

TABLE I-28

R F NHCHO Cl NHC(O)CH₃ Br NHCO₂CH₂Ph I NHCO₂CH₃ NH₂ NHCO₂CH₂CH₃NH(CO₂—t-Bu) NH(CO₂—i-Pr)

TABLE I-28a

R F NHCHO Cl NHC(O)CH₃ Br NHCOCH₂Ph I NHCO₂CH₃ NH₂ NHCO₂CH₂CH₃NH(CO₂—t-Bu) NH(CO₂—i-Pr)

TABLE I-28b

R F NHCHO Cl NHC(O)CH₃ Br NHCO₂CH₂Ph I NHCO₂CH₃ NH₂ NHCO₂CH₂CH₃NH(CO₂—t-Bu) NH(CO₂—i-Pr)

TABLE I-28c

R F NHCHO Cl NHC(O)CH₃ Br NHCO₂CH₂Ph I NHCO₂CH₃ NH₂ NHCO₂CH₂CH₃NH(CO₂—t-Bu) NH(CO₂—i-Pr)

TABLE I-28d

R F NHCHO Cl NHC(O)CH₃ Br NHCO₂CH₂Ph I NHCO₂CH₃ NH₂ NHCO₂CH₂CH₃NH(CO₂—t-Bu) NH(CO₂—i-Pr)

TABLE I-28e

R F NHCHO Cl NHC(O)CH₃ Br NHCO₂CH₂Ph I NHCO₂CH₃ NH₂ NHCO₂CH₂CH₃NH(CO₂—t-Bu) NH(CO₂—i-Pr)

TABLE I-28f

R F NHCHO Cl NHC(O)CH₃ Br NHCO₂CH₂Ph I NHCO₂CH₃ NH₂ NHCO₂CH₂CH₃NH(CO₂—t-Bu) NH(CO₂—i-Pr)

TABLE I-28g

R F NHCHO Cl NHC(O)CH₃ Br NHCO₂CH₂Ph I NHCO₂CH₃ NH₂ NHCO₂CH₂CH₃NH(CO₂—t-Bu) NH(CO₂—i-Pr)

TABLE I-29

R^(x) R^(y) R is Et H CF₃ Me CF₃ H Et Me Et H 3-pyridinyl Me 3-pyridinylH 6-fluoro-3-pyridinyl Me 6-fluoro-3-pyridinyl H 6-bromo-3-pyridinyl Me6-bromo-3-pyridinyl H 2-methyl-5-thiazolyl Me 2-methyl-5-thiazolyl H2-chloro-5-thiazolyl Me 2-chloro-5-thiazolyl H 1-methyl-4-pyrazolyl Me1-methyl-4-pyrazolyl H 5-pyrimidinyl Me 5-pyrimidinyl H CH₂CHFCF₂Cl MeCH₂CHFCF₂Cl H cyclopropyl Me cyclopropyl H 6-methyl-3-pyridinyl Me6-methyl-3-pyridinyl H 6-chloro-3-pyridinyl Me 6-chloro-3-pyridinyl H5-thiazolyl Me 5-thiazolyl H 2-fluoro-5-thiazolyl Me2-fluoro-5-thiazolyl H 2-bromo-5-thiazolyl Me 2-bromo-5-thiazolyl H3-methyl-5-isoxazolyl Me 3-methyl-5-isoxazolyl H 2-methyl-5-pyrimidinylMe 2-methyl-5-pyrimidinyl R is CH₂CHF₂ H CF₃ Me CF₃ H Et Me Et H3-pyridinyl Me 3-pyridinyl H 6-fluoro-3-pyridinyl Me6-fluoro-3-pyridinyl H 6-bromo-3-pyridinyl Me 6-bromo-3-pyridinyl H2-methyl-5-thiazolyl Me 2-methyl-5-thiazolyl H 2-chloro-5-thiazolyl Me2-chloro-5-thiazolyl H 1-methyl-4-pyrazolyl Me 1-methyl-4-pyrazolyl H5-pyrimidinyl Me 5-pyrimidinyl H CH₂CHFCF₂Cl Me CH₂CHFCF₂Cl Hcyclopropyl Me cyclopropyl H 6-methyl-3-pyridinyl Me6-methyl-3-pyridinyl H 6-chloro-3-pyridinyl Me 6-chloro-3-pyridinyl H5-thiazolyl Me 5-thiazolyl H 2-fluoro-5-thiazolyl Me2-fluoro-5-thiazolyl H 2-bromo-5-thiazolyl Me 2-bromo-5-thiazolyl H3-methyl-5-isoxazolyl Me 3-methyl-5-isoxazolyl H 2-methyl-5-pyrimidinylMe 2-methyl-5-pyrimidinyl

TABLE I-30 2-chloro-6-(trifluoromethyl)pyridine2-bromo-6-(trifluoromethyl)pyridine 2-iodo-6-(trifluoromethyl)pyridine4-chloro-2-fluoropyridine 4-bromo-2-fluoropyridine2-fluoro-4-iodopyridine 2-bromo-4-chloropyridine 2,4-dibromopyridine2-bromo-4-iodopyridine 4-chloro-2-(trifluoromethyl)pyridine4-bromo-2-(trifluoromethyl)pyridine 4-iodo-2-(trifluoromethyl)pyridine2,4-dichloropyridine 4-bromo-2-chloropyridine 2-chloro-4-iodopyridine

It is recognized that some reagents and reaction conditions describedabove for preparing compounds of Formula 1 may not be compatible withcertain functionalities present in the intermediates. In theseinstances, the incorporation of protection/deprotection sequences orfunctional group interconversions into the synthesis will aid inobtaining the desired products. The use and choice of the protectinggroups will be apparent to one skilled in chemical synthesis (see, forexample, Greene, T. W.; Wuts, P. G. M. Protective Groups in OrganicSynthesis, 2nd ed.; Wiley: New York, 1991). One skilled in the art willrecognize that, in some cases, after the introduction of a given reagentas it is depicted in any individual scheme, it may be necessary toperform additional routine synthetic steps not described in detail tocomplete the synthesis of compounds of Formula 1. One skilled in the artwill also recognize that it may be necessary to perform a combination ofthe steps illustrated in the above schemes in an order other than thatimplied by the particular sequence presented to prepare the compounds ofFormula 1.

One skilled in the art will also recognize that compounds of Formula 1and the intermediates described herein can be subjected to variouselectrophilic, nucleophilic, radical, organometallic, oxidation, andreduction reactions to add substituents or modify existing substituents.

Without further elaboration, it is believed that one skilled in the artusing the preceding description can utilize the present invention to itsfullest extent. The following Synthesis Examples are, therefore, to beconstrued as merely illustrative, and not limiting of the disclosure inany way whatsoever. Steps in the following Synthesis Examples illustratea procedure for each step in an overall synthetic transformation, andthe starting material for each step may not have necessarily beenprepared by a particular preparative run whose procedure is described inother Examples or Steps. Ambient or room temperature is defined as about20-25° C. Percentages are by weight except for chromatographic solventmixtures or where otherwise indicated. Parts and percentages forchromatographic solvent mixtures are by volume unless otherwiseindicated. MPLC refers to medium pressure liquid chromatography onsilica gel. ¹H NMR spectra are reported in ppm downfield fromtetramethylsilane; “s” means singlet, “d” means doublet, “dd” meansdoublet of doublets, “ddd” means doublet of doublet of doublets, “t”means triplet, “m” means multiplet, and “br s” means broad singlet. Formass spectral data, the numerical value reported is the molecular weightof the parent molecular ion (M) formed by addition of H⁺ (molecularweight of 1) to the molecule to give a M+1 peak observed by massspectrometry using atmospheric pressure chemical ionization (AP⁺).

Synthesis Example 1 Preparation of1-[(2-chloro-5-thiazolyl)methyl]-2-hydroxy-4-oxo-9-phenyl-3-[3-(trifluoromethoxy)phenyl]-4H-pyrido[1,2-a]pyrimidiniuminner salt (compound number 68) Step A: Preparation of2-amino-3-phenylpyridine

A microwave vial was charged with 2-amino-3-bromopyridine (0.5 g, 2.9mmol), phenylboronic acid (0.52 g, 4.3 mmol), sodium bicarbonate (0.31g, 2.9 mmol), dichlorobis(triphenylphosphine)palladium(II) (0.1 g, 0.14mmol), dioxane (5 mL) and water (1 mL). The vial was capped, and thereaction mixture was heated at 150° C. for 10 min. The reaction mixturewas then cooled, quenched with water (10 mL), and extracted twice withethyl acetate. The combined organic phases were dried (MgSO₄) andconcentrated to leave a black oil. The crude product was purified bychromatography on silica gel using 10-40% ethyl acetate/hexanes aseluant to provide the title compound as a white solid (0.35 g).

¹H NMR (CDCl₃) δ 8.10 (d, 1H), 7.46 (m, 4H), 7.38 (m, 2H), 6.75 (m, 1H),4.50-4.55 (br s, 2H).

Step B: Preparation ofN-[(2-chloro-5-thiazolyl)methylene]-3-phenyl-2-pyridinamine

2-Amino-3-phenylpyridine (i.e. the product of Step A, 0.342 g, 2.01mmol) was added to 2-chloro-1,3-thiazole-5-carbaldehyde (0.296 g, 2.01mmol) in dichloromethane (10 mL) at room temperature. The suspension wasstirred for 10 min and then concentrated to dryness under vacuum. Theresulting residue was heated to 90° C. for 20 min on a rotory evaporatorwith a non-returning bump trap to facilitate water removal. The residualyellow solid was again dissolved in dichloromethane (10 mL) and heatedto 90° C. on a rotory evaporator for an additional 20 min. At this timethe yellow solid was checked by NMR to verify reaction completion. Thetitle compound was obtained as a yellow solid and used in the next stepwithout further purification.

¹H NMR (CDCl₃) δ 9.29 (s, 1H), 8.45 (m, 1H), 7.92 (s, 1H), 7.80 (dd,1H), 7.50-7.35 (m, 5H), 7.30-7.25 (m, 1H).

Step C: Preparation ofN-[(2-chloro-5-thiazolyl)methyl]-3-phenyl-2-pyridinamine

N-[(2-chloro-5-thiazolyl)methylene]-3-phenyl-2-pyridinamine (i.e. theproduct of Step B) was added portionwise to a stirred excess of sodiumborohydride (0.379 g, 10.0 mmol) in methanol (8 mL). After addition wascomplete, the reaction mixture was allowed to stir for 5 min at ambienttemperature. The excess reducing agent was quenched by adding glacialacetic acid until gas evolution ceased. Water (20 mL) was added, and thereaction mixture was concentrated to remove methanol. The resultingaqueous phase was extracted twice with ethyl acetate, and the combinedorganic phases were dried (MgSO₄) and concentrated to give the titlecompound as a yellow solid (0.659 g).

¹H NMR (CDCl₃) δ 8.2 (d, 1H), 7.5-7.3 (m, 7H), 6.8-6.7 (m, 1H), 5.0-4.9(br s, 1H), 4.68 (d, 2H).

Step D: Preparation of1-[(2-chloro-5-thiazolyl)methyl]-2-hydroxy-4-oxo-9-phenyl-3-[3-(trifluoromethoxy)phenyl]-4H-pyrido[1,2-a]pyrimidiniuminner salt

N-[(2-chloro-5-thiazolyl)methyl]-3-phenyl-2-pyridinamine (i.e. theproduct of Step C, 100 mg, 0.33 mmol) and1,3-bis(2,4,6-trichlorophenyl)-2-[3-(trifluoromethoxy)phenyl]propanedioate(246 mg, 0.398 mmol) were dissolved in toluene (10 mL) and heated at 85°C. overnight. The reaction mixture was then poured onto a silica gelcolumn which was eluted with 50-100% ethyl acetate in hexanes to providethe title compound, a compound of the present invention, as a yellowsolid (63 mg).

¹H NMR (CDCl₃) δ 9.60 (d, 1H), 8.05 (d, 1H), 7.85-7.75 (m, 2), 7.55 (m,3H), 7.5-7.4 (m, 4H), 7.1 (dd, 1H), 6.84 (s, 1H), 5.1-5.25 (br s, 2H).

Synthesis Example 2 Preparation of1-[(2-chloro-5-thiazolyl)methyl]-3-(2-fluorophenyl)-2-hydroxy-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidiniuminner salt (compound number 30) Step A: Preparation ofN-[(2-chloro-5-thiazolyl)methyl]-3-methyl-2-pyridinamine

A mixture of 2-amino-3-methylpyridine (2.16 g, 20 mmol) and2-chloro-5-(chloromethyl)thiazole (1.68 g, 10 mmol) inN-methylpyrrolidinone (10 mL) was heated at 180° C. in a microwavereactor for 10 min. The cooled reaction mixture was poured into asaturated aqueous sodium bicarbonate solution and extracted with ethylacetate. The organic layer was separated, washed with saturated aqueoussodium bicarbonate solution, dried over Na₂SO₄, and concentrated underreduced pressure. The residue was purified by chromatography on silicagel eluted with 10% ethyl acetate in hexanes to provide the titlecompound as an oil (2.0 g).

¹H NMR (CDCl₃) δ 8.07 (d, 1H), 7.43 (s, 1H), 7.26 (d, 1H), 6.63 (dd,1H), 4.77 (d, 2H), 4.54 (br s, 1H).

Step B: Preparation of1,3-bis(2,4,6-trichlorophenyl)2-(2-fluorophenyl)propanedioate

To a solution of 2-(2-fluorophenyl)propanedioic acid (0.60 g, 3 mmol,prepared by the method described in Eur. J. Biochem. 1992, 210, 475) indichloromethane (5 mL) was added oxalyl chloride (0.65 mL, 7.5 mmol) andone drop of N,N-dimethylformamide. The reaction mixture was stirred for1 h at room temperature. 2,4,6-Trichlorophenol (1.47 g, 7.5 mmol) wasthen added, and the reaction mixture was stirred at room temperatureovernight. The reaction mixture was concentrated under reduced pressure,and the crude residue was triturated with a small amount of coldmethanol to yield the title compound as a white solid (1.1 g).

¹H NMR (CDCl₃) δ 7.73 (m, 1H), 7.42 (m, 1H), 7.37 (s, 2H), 7.24 (m, 1H),7.19 (t, 1H), 5.72 (s, 1H).

Step C: Preparation of1-[(2-chloro-5-thiazolyl)methyl]-3-(2-fluorophenyl)-2-hydroxy-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidiniuminner salt

A solution of N-[(2-chloro-5-thiazolyl)methyl]-3-methyl-2-pyridinamine(i.e. the product of Step A, 100 mg, 0.4 mmol) and1,3-bis(2,4,6-trichlorophenyl)2-(2-fluorophenyl)propanedioate (i.e. theproduct of Step B, 300 mg, 0.5 mmol) in toluene (1 mL) was heated at 70°C. for 1 h. The reaction mixture was then cooled and filtered, and thefiltered solid was triturated with a small amount of diethyl ether toyield the title product, a compound of the present invention, as ayellow solid (60 mg).

¹H NMR (CDCl₃) δ 9.52 (d, 1H), 8.01 (dd, 1H), 7.58 (t, 1H), 7.37 (t,1H), 7.1-7.35 (m, 4H), 5.62 (s, 2H), 2.84 (s, 3H).

Synthesis Example 2a

Alternative preparation of1-[(2-chloro-5-thiazolyl)methyl]-3-(2-fluorophenyl)-2-hydroxy-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidiniuminner salt (compound number 30)

Step A: Preparation of methyl α-cyano-2-fluorobenzeneacetate

Sodium methoxide (51.84 g) was added to dry toluene (815 mL) in a 1 Lreactor under a nitrogen atmosphere. The reaction mixture was heated to75° C., and then a mixture of 2-fluorobenzeneacetonitrile (100 g) indimethyl carbonate (131.64 g) was added at 70-74° C. over a period of 45minutes. The reaction mixture was further maintained at this temperature(70-75° C.) for an additional 4.5 hours. The reaction mixture was thencooled to 25-30° C. and added to a mixture of HCl (110 g, 35.2 wt %)diluted with water (300 mL) at 10-15° C. using an addition funnel. Theresulting layers were separated, and the aqueous layer was extractedwith ethyl acetate (2×200 mL). The combined organic layers were washedwith water (2×200 mL), dried over sodium sulfate, and concentrated underreduced pressure to provide the title compound as a brown oily liquid(138.8 g, 94.8% yield).

Step B: Preparation of 1,3-dimethyl 2-(2-fluorophenyl)propanedioate

Methyl α-cyano-2-fluorobenzeneacetate (135 g) was added to methanol (675g) in a 1 L reactor under nitrogen atmosphere. The reaction mixture wascooled to 0° C. and thionyl chloride (240.47 g) was added slowly over aperiod of 45 minutes. The reaction mixture was heated to 45° C. for 19hours, and the progress of the reaction was monitored by HPLC. Thereaction mixture was then cooled to 30° C., and concentrated underreduced pressure at 45-47° C. The residue was dissolved in water (300mL) and extracted with ethyl acetate (2×300 mL). The combined organiclayers were washed with water (2×300 mL), dried over sodium sulfate, andconcentrated under reduced pressure to dryness to give the titlecompound (152.2 g, 95.9% yield).

Step C: Preparation of 2-(2-fluorophenyl)propanedioic acid

Sodium hydroxide (117.11 g of a 50% aqueous solution) was added to water(160.5 g), and the solution was cooled to 10-15° C. Tetramethylammoniumchloride (4.88 g) was added, followed by the dropwise addition of1,3-dimethyl 2-(2-fluorophenyl)propanedioate (150 g) over a period of 30minutes at 10-15° C. The temperature of the reaction was slowly raisedto 30° C. after the addition and maintained at 27-32° C. The reactionmass became a thick slurry, and water (25 g) was added to improvestirring. The progress of the reaction was monitored by HPLC. Afterstirring for 2 hours, the reaction mixture was added to a solution ofHCl (231 g) and water (150 mL) over a period of 30 minutes at 5-10° C.The pH of the mixture was adjusted to <2, and the reaction mixture wasstirred at 5-10° C. for half an hour. The reaction mixture was thenfiltered to isolate a solid product that was air dried, and then furtherdried under reduced pressure at 35° C. for 3 hours. The dried solid wasslurried with petroleum ether, and the slurry was filtered to reisolatedthe solid. The solid was then dried under reduced pressure at 35° C. for3 hours to give the title product (115.5 g, 93.97%).

Step D: Preparation of1,3-bis(4-nitrophenyl)2-(2-fluorophenyl)propanedioate

To a 1 L flask was added toluene (500 mL),2-(2-fluorophenyl)propanedioic acid (100 g, 0.479 moles) andN,N-dimethylformamide (6.92 g) at 25° C. under a nitrogen atmosphere.The reaction mixture was initially heated to 30° C. and thionyl chloride(127.53 g, 1.071 moles) was added dropwise over a period of 20 minutesat 25-30° C. After the addition, the reaction mixture was heated to48-50° C. and this temperature maintained for 3.5 hours. Toluene (300mL) was then added to the reaction mixture in one portion, followed bythe addition of solid 4-nitrophenol (148.09 g total, 1.064 moles) in tenportions over a period of 15 minutes. After the addition, the reactionmixture was maintained at 49-55° C. for 1.5 hours. The reaction mixturewas then concentrated under reduced pressure at 40-45° C. to removetoluene. The resulting residue was triturated using cold methanol (300mL, approximately 5° C.) to yield an off-white solid which was isolatedby filtration, washed with cold methanol (2×150 mL, approximately 5° C.)and dried under reduced pressure at 45° C. to give the title compound(163.8 g, 71.6%).

Step E: Preparation of1-[(2-chloro-5-thiazolyl)methyl]-3-(2-fluorophenyl)-2-hydroxy-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidiniuminner salt

N-[(2-chloro-5-thiazolyl)methyl]-3-methyl-2-pyridinamine (i.e. theproduct of Example 2 Step A, 60.0 g, 0.247 mol), 1,3-bis(4-nitrophenyl)2-(2-fluorophenyl)propanedioate (142 g, 0.297 mol), imidazole (6.74 g,99 mmol), and ethyl acetate (300 mL) were added to a reactor, and thereaction mixture was heated to 72-77° C. for 2.0 hours. The reactionmixture was then cooled to 40° C., and water (460 mL) was added. Theresulting slurry was cooled to 10° C. and further maintained at thattemperature for 15 minutes. The slurry was then filtered to isolate awet solid which was washed with methanol (360 mL). The crude product wasair dried, and then dried further under reduced pressure at 45-50° C.for 3 hours to provide the title compound, a compound of this invention,as a solid (93.7 g, 93.1% yield). ¹H NMR (dmso-d₆) δ 9.26 (d, 1H), 8.27(d, 1H), 7.78 (s, 1H), 7.57-7.46 (m, 2H), 7.33-7.29 (m, 1H), 7.21-7.15(m, 2H), 5.44 (s, 2H), 2.72 (s, 3H).

Synthesis Example 3 Preparation of1-[(2-chloro-5-thiazolyl)methyl]-3-(2′,3′-dichloro-[1,1′-biphenyl]-3-yl)-2-hydroxy-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidiniuminner salt (compound number 88) Step A: Preparation of2′,3′-dichloro-[1,1′-biphenyl]-3-acetic acid ethyl ester

A mixture of 3-iodobenzeneacetic acid ethyl ester (0.87 g, 3 mmol,prepared by the method described in J. Chem. Soc. 1963, 5437),2,3-dichlorophenylboronic acid (0.85 g, 4.5 mmol),bis(triphenylphosphine)palladium dichloride (0.10 g, 0.15 mmol) and 2 Naqueous sodium bicarbonate solution (3 mL) in p-dioxane (6 mL) washeated at 160° C. in a microwave reactor for 5 min. The reaction mixturewas cooled, poured into water, and extracted with ethyl acetate. Theorganic layer was separated, washed with brine, dried over Na₂SO₄, andconcentrated under reduced pressure. The residue was purified bychromatography on silica gel eluted with ethyl acetate in hexanes toprovide the title product (0.48 g).

¹H NMR (CDCl₃) δ 8.07 (d, 1H), 7.43 (s, 1H), 7.26 (d, 1H), 6.63 (dd,1H), 4.77 (d, 2H), 4.54 (br s, 1H).

Step B: Preparation of2-(2′,3′-dichloro-[1,1′-biphenyl]-3-yl)propanedioic acid 1,3-diethylester

To a solution of 2′,3′-dichloro-[1,1′-biphenyl]-3-acetic acid ethylester (i.e. the product of Step A, 0.45 g, 1.45 mmol) and diethylcarbonate (5 mL) was added sodium hydride (60% dispersion in oil, 0.23g, 5.8 mmol). The reaction mixture was stirred overnight at roomtemperature, and then quenched with saturated aqueous ammonium chloridesolution. The reaction mixture was then extracted with ethyl acetate,and the organic layer was dried over sodium sulfate and concentratedunder reduced pressure to yield the title compound (0.50 g).

¹H NMR (CDCl₃) δ 7.35-7.5 (m, 5H), 7.25 (t, 2H), 5.30 (s, 1H), 4.20 (q,4H), 1.26 (t, 6H).

Step C: Preparation of2-(2′,3′-dichloro[1,1′-biphenyl]-3-yl)propanedioic acid

2-(2′,3′-Dichloro-[1,1′-biphenyl]-3-yl)propanedioic acid 1,3-diethylester (i.e. the product of Step B, 0.30 g, 0.79 mmol) was added to 2%aqueous sodium hydroxide (5 mL), and the reaction mixture was heated at70° C. for 20 min. The reaction mixture was cooled, quenched with 6 Naqueous hydrochloric acid, and extracted with ethyl acetate. The organiclayer was separated, washed with brine, dried over sodium sulfate, andconcentrated under reduced pressure to yield the title compound (0.20g).

¹H NMR (CDCl₃) δ 7.4-7.5 (m, 5H), 7.20-7.25 (m, 2H), 4.74 (s, 1H).

Step D: Preparation of1-[(2-chloro-5-thiazolyl)methyl]-3-(2′,3′-dichloro[1,1′-biphenyl]-3-yl)-2-hydroxy-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidiniuminner salt

To a solution of 2-(2′,3′-dichloro[1,1′-biphenyl]-3-yl)propanedioic acid(i.e. the product of Step C, 200 mg, 0.62 mmol) in dichloromethane (3mL) was added one drop of N,N-dimethylformamide and oxalyl chloride (0.3mL, 3.5 mmol). The reaction mixture was stirred at room temperature for30 min, and concentrated under reduced pressure. The residue wasredissolved in dichloromethane (3 mL), and this solution was added to anice-cooled solution ofN-[(2-chloro-5-thiazolyl)methyl]-3-methyl-2-pyridinamine (i.e. theproduct of Synthesis Example 2 Step A, 100 mg, 0.44 mmol) andtriethylamine (0.3 mL, 2.2 mmol) in dichloromethane (2 mL). The reactionmixture was stirred with cooling for 15 min and then concentrated in thepresence of a small amount of Celite® diatomaceous filter aid. The cruderesidue was purified by MPLC to yield 88 mg of the title compound, acompound of the present invention.

¹H NMR (CDCl₃) δ 9.52 (d, 1H), 8.04 (dd, 1H), 7.76 (d, 1H), 7.2-7.45 (m,6H), 5.95 (m, 1H), 5.34 (d, 1H), 5.30 (d, 1H), 5.01 (d, 2H).

Synthesis Example 4 Preparation of1-[(2-chloro-5-thiazolyl)methyl]-2-hydroxy-4-oxo-3-phenyl-4H-pyrimido[2,1-a]isoquinoliniuminner salt (compound number 99) Step A: Preparation ofN-[(2-chloro-5-thiazolyl)methyl]-1-isoquinolinamine

A mixture of 1-aminoisoquinoline (0.56 g, 3.9 mmol) and2-chloro-5-(chloromethyl)thiazole (0.50 g, 3.0 mmol) inN-methylpyrrolidinone (3 mL) was heated to 220° C. in a microwavereactor for 10 min. The reaction mixture was cooled to room temperature,diluted with water (20 mL), and extracted with diethyl ether (5×20 mL).The combined organic extracts were concentrated under reduced pressure,and the resulting residue was purified by chromatography on silica geleluted with 20-50% ethyl acetate/hexane to give the title compound as apale yellow solid (0.09 g).

¹H NMR (CDCl₃) δ 8.07 (d, 1H), 7.70-7.75 (m, 2H), 7.62 (t, 1H), 7.50 (t,1H), 7.05 (d, 1H), 5.60 (br s, 1H), 4.91 (d, 2H), 1.58 (br s, NH+H₂O).

Step B: Preparation of1-[(2-chloro-5-thiazolyl)methyl]-2-hydroxy-4-oxo-3-phenyl-4H-pyrimido[2,1-a]isoquinoliniuminner salt

To a solution of phenylmalonic acid (0.44 g, 2.4 mmol) indichloromethane (10 mL) was added two drops of N,N-dimethylformamide andoxalyl chloride (1.1 mL, 12 mmol). The reaction mixture was stirred atroom temperature for 30 min, concentrated under reduced pressure, andthen redissolved in dichloromethane (2.4 mL). A portion of the resultingsolution (0.4 mL, 0.4 mmol) was added to an ice-cooled solution ofN-[(2-chloro-5-thiazolyl)methyl]-1-isoquinolinamine (i.e. the product ofStep A, 50 mg, 0.18 mmol) and triethylamine (0.08 mL) in dichloromethane(2 mL). The reaction mixture was allowed to warm to room temperature andstirred overnight. The reaction mixture was then concentrated, and thecrude residue was purified by MPLC (80-100% ethyl acetate/hexane aseluant) to yield 17.4 mg of the title compound, a compound of thepresent invention.

¹H NMR (CDCl₃) δ 9.26 (d, 1H), 8.65 (d, 1H), 7.97-8.02 (m, 2H), 7.84 (d,2H), 7.78-7.82 (m, 1H), 7.68 (s, 1H), 7.60 (d, 1H), 7.42-7.48 (m, 3H),5.64 (br s, 2H).

Synthesis Example 5 Preparation of2-hydroxy-9-methyl-4-oxo-1-(5-pyrimidinylmethyl)-3-[3-(trifluoromethoxy)phenyl]-4H-pyrido[1,2-a]pyrimidiniuminner salt (compound number 43) Step A: Preparation ofN-(5-pyrimidinylmethyl)-3-methyl-2-pyridinamine

To a solution of 5-pyrimidinecarboxaldehyde (5.0 g, 46 mmol) in toluene(100 mL) was added 2-amino-3-picoline (5.0 g, 46 mmol). The reactionmixture was heated to 80° C. on a rotary evaporator while under reducedpressure. After 10 min an additional 200 mL of toluene was added.Continued heating under reduced pressure resulted in a white solid whichwas dissolved in methanol (200 mL). This solution was stirred vigorouslyunder a nitrogen atmosphere, and granular sodium borohydride (10.0 g,265 mmol) was added portionwise, resulting in vigorous bubbling. Thereaction was allowed to stir for 1 h at room temperature aftercompletion of the sodium borohydride addition. Acetic acid (1 mL) wasthen added, and the reaction mixture was stirred for 5 min, followed bythe addition of water (100 mL). The volatiles were removed under reducedpressure, and the aqueous suspension was extracted with dichloromethane(2×100 mL). The organic layers were combined and dried over MgSO₄,filtered, and the solvent was removed under reduced pressure to yield anoff-white solid. The crude solid was adsorbed onto Celite® and purifiedby column chromatography (gradient of 100% hexanes to 100% ethyl acetateover 30 minutes) to yield 8.848 g of a white solid.

¹H NMR (CDCl₃) δ 9.11 (s, 1H), 8.77 (s, 2H), 8.00 (d, 1H), 7.26 (s, 1H),6.60 (dd, 1H), 4.73 (d, 2H), 4.59 (br s, NH), 2.12 (s, 3H).

Step B: Preparation of2-hydroxy-9-methyl-4-oxo-1-(5-pyrimidinylmethyl)-3-[3-(trifluoromethoxy)phenyl]-4H-pyrido[1,2-a]pyrimidiniuminner salt

To a solution of1,3-bis(2,4,6-trichlorophenyl)-2-[3-(trifluoromethoxy)phenyl]-propanedioicacid ester (100 mg, 0.16 mmoles) in toluene (10 mL) was addedN-(5-pyrimidinylmethyl)-3-methyl-2-pyridinamine (i.e. the product ofStep A, 32 mg, 0.16 mmoles). The reaction mixture was heated to 80° C.for 18 h. Cooling of the reaction vessel to 0° C. resulted in theprecipitation of a yellow solid which was isolated by filtration toprovide 13.2 mg of the title compound, a compound of the presentinvention, as a yellow solid.

¹H NMR (CD₃C(O)CD₃) δ 9.46 (d, 1H), 9.05 (s, 1H), 8.83 (s, 2H) 8.27 (d,1H), 8.04 (d, 1H), 8.02 (s, 1H), 7.57 (t, 1H), 7.38 (t, 1H), 7.07 (d,1H), 5.66 (s, 2H), 2.69 (s, 3H).

By the procedures described herein together with methods known in theart, the following compounds of Tables 1 to 32 can be prepared. Thefollowing abbreviations are used in Tables 1 to 32 which follow: Memeans methyl, Et means ethyl, Pr means propyl and Ph means phenyl.

Tables 1-15 pertain to the structure of Formula T-1 shown below.

TABLE 1 T-1

R^(b), R^(c), R^(d), R^(e), R^(3a), R^(3b) and R^(3c) are H; R^(3d) isMe; R² is 2-chloro-5-thiazolyl R^(a) H F Cl Br I Me Et Pr i-Pr c-Pr t-BuCF₃ CH₂F CHF₂ OMe OEt O—n-Pr OPh CH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂OCH₂C≡CH O—c-Pr OCF₃ OCHF₂ OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂MeCO₂Et cyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl3-chlorophenyl 3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl4-fluorophenyl 4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(a), R^(c), R^(d), R^(e), R^(3a),R^(3b) and R^(3c) are H; R^(3d) is Me; R² is 2-chloro-5-thiazolyl R^(b)H F Cl Br I Me Et Pr i-Pr c-Pr t-Bu CF₃ CH₂F CHF₂ OMe OEt O—n-Pr OPhCH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂ OCH₂C≡CH O—c-Pr OCF₃ OCHF₂ OCH₂CF₃SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Et cyano C(O)NHMe C(O)NMe₂C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl 3-chlorophenyl 3-(CF₃)phenyl3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl 4-fluorophenyl4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(a), R^(b), R^(d), R^(e), R^(3a),R^(3b) and R^(3c) are H; R^(3d) is Me; R² is 2-chloro-5-thiazolyl R^(c)H F Cl Br I Me Et Pr i-Pr c-Pr t-Bu CF₃ CH₂F CHF₂ OMe OEt O—n-Pr OPhCH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂ OCH₂C≡CH O—c-Pr OCF₃ OCHF₂ OCH₂CF₃SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Et cyano C(O)NHMe C(O)NMe₂C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl 3-chlorophenyl 3-(CF₃)phenyl3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl 4-fluorophenyl4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(a) is F; R^(c), R^(d), R^(e,)R^(3a), R^(3b) and R^(3c) are H; R^(3d) is Me; R² is2-chloro-5-thiazolyl R^(b) H F Cl Br I Me Et Pr i-Pr c-Pr t-Bu CF₃ CH₂FCHF₂ OMe OEt O—n-Pr OPh CH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂ OCH₂C≡CHO—c-Pr OCF₃ OCHF₂ OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Etcyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl3-chlorophenyl 3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl4-fluorophenyl 4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(a) is F; R^(b), R^(d), R^(e),R^(3a), R^(3b) and R^(3c) are H; R^(3d) is Me; R² is2-chloro-5-thiazolyl R^(c) H F Cl Br I Me Et Pr i-Pr c-Pr t-Bu CF₃ CH₂FCHF₂ OMe OEt O—n-Pr OPh CH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂ OCH₂C≡CHO—c-Pr OCF₃ OCHF₂ OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Etcyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl3-chlorophenyl 3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl4-fluorophenyl 4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(a) is F; R^(b), R^(c), R^(e),R^(3a), R^(3b) and R^(3c) are H; R^(3d) is Me; R² is2-chloro-5-thiazolyl R^(d) H F Cl Br I Me Et Pr i-Pr c-Pr t-Bu CF₃ CH₂FCHF₂ OMe OEt O—n-Pr OPh CH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂ OCH₂C≡CHO—c-Pr OCF₃ OCHF₂ OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Etcyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl3-chlorophenyl 3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl4-fluorophenyl 4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(a) is F; R^(b), R^(c), R^(d),R^(3a), R^(3b) and R^(3c) are H; R^(3d) is Me; R² is2-chloro-5-thiazolyl R^(e) H F Cl Br I Me Et Pr i-Pr c-Pr t-Bu CF₃ CH₂FCHF₂ OMe OEt O—n-Pr OPh CH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂ OCH₂C≡CHO—c-Pr OCF₃ OCHF₂ OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Etcyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl3-chlorophenyl 3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl4-fluorophenyl 4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(a) is Cl; R^(c), R^(d), R^(e),R^(3a), R^(3b) and R^(3c) are H; R^(3d) is Me; R² is2-chloro-5-thiazolyl R^(b) H F Cl Br I Me Et Pr i-Pr c-Pr t-Bu CF₃ CH₂FCHF₂ OMe OEt O—n-Pr OPh CH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂ OCH₂C≡CHO—c-Pr OCF₃ OCHF₂ OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Etcyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl3-chlorophenyl 3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl4-fluorophenyl 4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(a) is Cl; R^(b), R^(d), R^(e),R^(3a), R^(3b) and R^(3c) are H; R^(3d) is Me; R² is2-chloro-5-thiazolyl R^(c) H F Cl Br I Me Et Pr i-Pr c-Pr t-Bu CF₃ CH₂FCHF₂ OMe OEt O—n-Pr OPh CH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂ OCH₂C≡CHO—c-Pr OCF₃ OCHF₂ OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Etcyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl3-chlorophenyl 3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl4-fluorophenyl 4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(a) is Cl; R^(b), R^(c), R^(e),R^(3a), R^(3b) and R^(3c) are H; R^(3d) is Me; R² is2-chloro-5-thiazolyl R^(d) H F Cl Br I Me Et Pr i-Pr c-Pr t-Bu CF₃ CH₂FCHF₂ OMe OEt O—n-Pr OPh CH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂ OCH₂C≡CHO—c-Pr OCF₃ OCHF₂ OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Etcyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl3-chlorophenyl 3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl4-fluorophenyl 4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(a) is Cl; R^(b), R^(c), R^(d),R^(3a), R^(3b) and R^(3c) are H; R^(3d) is Me; R² is2-chloro-5-thiazolyl R^(e) H F Cl Br I Me Et Pr i-Pr c-Pr t-Bu CF₃ CH₂FCHF₂ OMe OEt O—n-Pr OPh CH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂ OCH₂C≡CHO—c-Pr OCF₃ OCHF₂ OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Etcyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl3-chlorophenyl 3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl4-fluorophenyl 4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(a) is OMe; R^(c), R^(d), R^(e),R^(3a), R^(3b) and R^(3c) are H; R^(3d) is Me; R² is2-chloro-5-thiazolyl R^(b) H F Cl Br I Me Et Pr i-Pr c-Pr t-Bu CF₃ CH₂FCHF₂ OMe OEt O—n-Pr OPh CH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂ OCH₂C≡CHO—c-Pr OCF₃ OCHF₂ OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Etcyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl3-chlorophenyl 3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl4-fluorophenyl 4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(a) is OMe; R^(b), R^(d), R^(e),R^(3a), R^(3b) and R^(3c) are H; R^(3d) is Me; R² is2-chloro-5-thiazolyl R^(c) H F Cl Br I Me Et Pr i-Pr c-Pr t-Bu CF₃ CH₂FCHF₂ OMe OEt O—n-Pr OPh CH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂ OCH₂C≡CHO—c-Pr OCF₃ OCHF₂ OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Etcyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl3-chlorophenyl 3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl4-fluorophenyl 4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(a) is OMe; R^(b), R^(c), R^(e),R^(3a), R^(3b) and R^(3c) are H; R^(3d) is Me; R² is2-chloro-5-thiazolyl R^(d) H F Cl Br I Me Et Pr i-Pr c-Pr t-Bu CF₃ CH₂FCHF₂ OMe OEt O—n-Pr OPh CH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂ OCH₂C≡CHO—c-Pr OCF₃ OCHF₂ OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Etcyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl3-chlorophenyl 3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl4-fluorophenyl 4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(a) is OMe; R^(b), R^(c), R^(d),R^(3a), R^(3b) and R^(3c) are H; R^(3d) is Me; R² is2-chloro-5-thiazolyl R^(e) H F Cl Br I Me Et Pr i-Pr c-Pr t-Bu CF₃ CH₂FCHF₂ OMe OEt O—n-Pr OPh CH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂ OCH₂C≡CHO—c-Pr OCF₃ OCHF₂ OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Etcyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl3-chlorophenyl 3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl4-fluorophenyl 4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(a) is Me; R^(c), R^(d), R^(e),R^(3a), R^(3b) and R^(3c) are H; R^(3d) is Me; R² is2-chloro-5-thiazolyl R^(b) H F Cl Br I Me Et Pr i-Pr c-Pr t-Bu CF₃ CH₂FCHF₂ OMe OEt O—n-Pr OPh CH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂ OCH₂C≡CHO—c-Pr OCF₃ OCHF₂ OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Etcyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl3-chlorophenyl 3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl4-fluorophenyl 4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(a) is Me; R^(b), R^(d,) R^(e),R^(3a), R^(3b) and R^(3c) are H; R^(3d) is Me; R² is2-chloro-5-thiazolyl R^(c) H F Cl Br I Me Et Pr i-Pr c-Pr t-Bu CF₃ CH₂FCHF₂ OMe OEt O—n-Pr OPh CH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂ OCH₂C≡CHO—c-Pr OCF₃ OCHF₂ OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Etcyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl3-chlorophenyl 3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl4-fluorophenyl 4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(a) is Me; R^(b), R^(c), R^(e),R^(3a), R^(3b) and R^(3c) are H; R^(3d) is Me; R² is2-chloro-5-thiazolyl R^(d) H F Cl Br I Me Et Pr i-Pr c-Pr t-Bu CF₃ CH₂FCHF₂ OMe OEt O—n-Pr OPh CH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂ OCH₂C≡CHO—c-Pr OCF₃ OCHF₂ OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Etcyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl3-chlorophenyl 3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl4-fluorophenyl 4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(a) is Me; R^(b), R^(c), R^(d),R^(3a), R^(3b) and R^(3c) are H; R^(3d) is Me; R² is2-chloro-5-thiazolyl R^(e) H F Cl Br I Me Et Pr i-Pr c-Pr t-Bu CF₃ CH₂FCHF₂ OMe OEt O—n-Pr OPh CH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂ OCH₂C≡CHO—c-Pr OCF₃ OCHF₂ OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Etcyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl3-chlorophenyl 3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl4-fluorophenyl 4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(d) is Cl; R^(a), R^(c), R^(e),R^(3a), R^(3b) and R^(3c) are H; R^(3d) is Me; R² is2-chloro-5-thiazolyl R^(b) H F Cl Br I Me Et Pr i-Pr c-Pr t-Bu CF₃ CH₂FCHF₂ OMe OEt O—n-Pr OPh CH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂ OCH₂C≡CHO—c-Pr OCF₃ OCHF₂ OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Etcyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl3-chlorophenyl 3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl4-fluorophenyl 4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(d) is CF₃; R^(a), R^(c), R^(e),R^(3a), R^(3b) and R^(3c) are H; R^(3d) is Me; R² is2-chloro-5-thiazolyl R^(b) H F Cl Br I Me Et Pr i-Pr c-Pr t-Bu CF₃ CH₂FCHF₂ OMe OEt O—n-Pr OPh CH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂ OCH₂C≡CHO—c-Pr OCF₃ OCHF₂ OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Etcyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl3-chlorophenyl 3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl4-fluorophenyl 4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(b) is Br; R^(a), R^(c), R^(e),R^(3a), R^(3b) and R^(3c) are H; R^(3d) is Me; R² is2-chloro-5-thiazolyl R^(d) H F Cl Br I Me Et Pr i-Pr c-Pr t-Bu CF₃ CH₂FCHF₂ OMe OEt O—n-Pr OPh CH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂ OCH₂C≡CHO—c-Pr OCF₃ OCHF₂ OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Etcyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl3-chlorophenyl 3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl4-fluorophenyl 4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(b) is OCF₃; R^(a), R^(c), R^(e),R^(3a), R^(3b) and R^(3e) are H; R^(3d) is Me; R² is2-chloro-5-thiazolyl R^(d) H F Cl Br I Me Et Pr i-Pr c-Pr t-Bu CF₃ CH₂FCHF₂ OMe OEt O—n-Pr OPh CH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂ OCH₂C≡CHO—c-Pr OCF₃ OCHF₂ OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Etcyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl3-chlorophenyl 3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl4-fluorophenyl 4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(b) is OMe; R^(a), R^(c), R^(e),R^(3a), R^(3b) and R^(3c) are H; R^(3d) is Me; R² is2-chloro-5-thiazolyl R^(d) H F Cl Br I Me Et Pr i-Pr c-Pr t-Bu CF₃ CH₂FCHF₂ OMe OEt O—n-Pr OPh CH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂ OCH₂C≡CHO—c-Pr OCF₃ OCHF₂ OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Etcyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl3-chlorophenyl 3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl4-fluorophenyl 4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(b) is F; R^(a) R^(c), R^(e), R^(3a),R^(3b) and R^(3c) are H; R^(3d) is Me; R² is 2-chloro-5-thiazolyl R^(d)H F Cl Br I Me Et Pr i-Pr c-Pr t-Bu CF₃ CH₂F CHF₂ OMe OEt O—n-Pr OPhCH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂ OCH₂C≡CH O—c-Pr OCF₃ OCHF₂ OCH₂CF₃SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Et cyano C(O)NHMe C(O)NMe₂C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl 3-chlorophenyl 3-(CF₃)phenyl3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl 4-fluorophenyl4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(b) is CN; R^(a), R^(c), R^(e),R^(3a), R^(3b) and R^(3c) are H; R^(3d) is Me; R² is2-chloro-5-thiazolyl R^(d) H F Cl Br I Me Et Pr i-Pr c-Pr t-Bu CF₃ CH₂FCHF₂ OMe OEt O—n-Pr OPh CH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂ OCH₂C≡CHO—c-Pr OCF₃ OCHF₂ OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Etcyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl3-chlorophenyl 3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl4-fluorophenyl 4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(b) is Me; R^(a), R^(c), R^(e),R^(3a), R^(3b) and R^(3c) are H; R^(3d) is Me; R² is2-chloro-5-thiazolyl R^(d) H F Cl Br I Me Et Pr i-Pr c-Pr t-Bu CF₃ CH₂FCHF₂ OMe OEt O—n-Pr OPh CH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂ OCH₂C≡CHO—c-Pr OCF₃ OCHF₂ OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Etcyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl3-chlorophenyl 3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl4-fluorophenyl 4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(b) is I; R^(a), R^(c), R^(e),R^(3a), R^(3b) and R^(3c) are H; R^(3d) is Me; R² is2-chloro-5-thiazolyl R^(d) H F Cl Br I Me Et Pr i-Pr c-Pr t-Bu CF₃ CH₂FCHF₂ OMe OEt O—n-Pr OPh CH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂ OCH₂C≡CHO—c-Pr OCF₃ OCHF₂ OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Etcyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl3-chlorophenyl 3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl4-fluorophenyl 4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(a) and R^(b) are F; R^(c), R^(e),R^(3a), R^(3b) and R^(3c) are H; R^(3d) is Me; R² is2-chloro-5-thiazolyl R^(d) H F Cl Br I Me Et Pr i-Pr c-Pr t-Bu CF₃ CH₂FCHF₂ OMe OEt O—n-Pr OPh CH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂ OCH₂C≡CHO—c-Pr OCF₃ OCHF₂ OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Etcyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl3-chlorophenyl 3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl4-fluorophenyl 4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(a) is F; R^(b) is Cl; R^(c), R^(e),R^(3a), R^(3b) and R^(3c) are H; R^(3d) is Me; R² is2-chloro-5-thiazolyl R^(d) H F Cl Br I Me Et Pr i-Pr c-Pr t-Bu CF₃ CH₂FCHF₂ OMe OEt O—n-Pr OPh CH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂ OCH₂C≡CHO—c-Pr OCF₃ OCHF₂ OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Etcyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl3-chlorophenyl 3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl4-fluorophenyl 4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(a) and R^(e) are F; R^(c), R^(d),R^(3a), R^(3b) and R^(3c) are H; R^(3d) is Me; R² is2-chloro-5-thiazolyl R^(b) H F Cl Br I Me Et Pr i-Pr c-Pr t-Bu CF₃ CH₂FCHF₂ OMe OEt O—n-Pr OPh CH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂ OCH₂C≡CHO—c-Pr OCF₃ OCHF₂ OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Etcyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl3-chlorophenyl 3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl4-fluorophenyl 4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(c) is OMe R^(a), R^(b), R^(e),R^(3a), R^(3b) and R^(3c) are H; R^(3d) is Me; R² is2-chloro-5-thiazolyl R^(d) H F Cl Br I Me Et Pr i-Pr c-Pr t-Bu CF₃ CH₂FCHF₂ OMe OEt O—n-Pr OPh CH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂ OCH₂C≡CHO—c-Pr OCF₃ OCHF₂ OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Etcyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl3-chlorophenyl 3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl4-fluorophenyl 4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(c) is Me; R^(a), R^(b), R^(e),R^(3a), R^(3b) and R^(3c) are H; R^(3d) is Me; R² is2-chloro-5-thiazolyl R^(d) H F Cl Br I Me Et Pr i-Pr c-Pr t-Bu CF₃ CH₂FCHF₂ OMe OEt O—n-Pr OPh CH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂ OCH₂C≡CHO—c-Pr OCF₃ OCHF₂ OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Etcyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl3-chlorophenyl 3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl4-fluorophenyl 4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(c) is F; R^(a), R^(b), R^(e),R^(3a), R^(3b) and R^(3c) are H; R^(3d) is Me; R² is2-chloro-5-thiazolyl R^(d) H F Cl Br I Me Et Pr i-Pr c-Pr t-Bu CF₃ CH₂FCHF₂ OMe OEt O—n-Pr OPh CH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂ OCH₂C≡CHO—c-Pr OCF₃ OCHF₂ OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Etcyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl3-chlorophenyl 3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl4-fluorophenyl 4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl R^(c) is Cl; R^(a), R^(b), R^(e),R^(3a), R^(3b) and R^(3c) are H; R³d is Me; R² is 2-chloro-5-thiazolylR^(d) H F Cl Br I Me Et Pr i-Pr c-Pr t-Bu CF₃ CH₂F CHF₂ OMe OEt O—n-PrOPh CH═CH₂ C≡CH phenyl O—i-Pr OCH₂CH═CH₂ OCH₂C≡CH O—c-Pr OCF₃ OCHF₂OCH₂CF₃ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Et cyano C(O)NHMeC(O)NMe₂ C(═NOMe)Me C(═NOEt)Me 2-fluorophenyl 3-chlorophenyl3-(CF₃)phenyl 3-fluorophenyl 3-cyanophenyl 3-(OCF₃)phenyl 4-fluorophenyl4-chlorophenyl 4-(CF₃)phenyl 4-cyanophenyl 4-bromophenyl6-chloro-3-pyridinyl 6-fluoro-3-pyridinyl 6-(CF₃)-3-pyridinyl4,6-dichloro-3-pyridinyl 2-fluoro-6-chloro-3-pyridinyl2,6-dichloro-3-pyridinyl 2-bromo-5-chloro-4-pyridinyl3-bromo-5-fluorophenyl 3-chloro-5-fluorophenyl 3-fluoro-4-chlorophenyl2,4-dichlorophenyl 2,4-difluorophenyl 2-fluoro-4-cyanophenyl2-fluoro-4-chlorophenyl 2-methyl-4-chlorophenyl 2-fluoro-4-(CF₃)phenyl2,4-bis(CF₃)phenyl 2-fluoro-4-bromophenyl 2-chloro-4-fluorophenyl2-(CF₃)-4-fluorophenyl 2-methyl-4-(CF₃)phenyl 2-chloro-4-(CF₃)phenyl2-(CF₃)-4-chlorophenyl 2,5-difluorophenyl 2-fluoro-5-(CF₃)phenyl2-fluoro-5-chlorophenyl 2,5-dichlorophenyl 2-fluoro-5-(OCF₃)phenyl2-chloro-5-(CF₃)phenyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl

Table 2

Table 2 is identical to Table 1, except that R^(3d) is OMe. For example,the first compound in Table 2 is the compound of Formula T-1 whereinR^(a), R^(b), R^(c), R^(d), R^(e), R^(3a), R^(3b) and R^(3c) are H;R^(3d) is OMe; and R² is 2-chloro-5-thiazolyl.

Table 2a

Table 2a is identical to Table 1, except that R^(3d) is Et. For example,the first compound in Table 2a is the compound of Formula T-1 whereinR^(a), R^(b), R^(c), R^(d), R^(e), R^(3a), R^(3b) and R^(3c) are H;R^(3d) is Et; and R² is 2-chloro-5-thiazolyl.

Table 3

Table 3 is identical to Table 1, except that R^(3d) is Cl. For example,the first compound in Table 3 is the compound of Formula T-1 whereinR^(a), R^(b), R^(c), R^(d), R^(e), R^(3a), R^(3b) and R^(3c) are H;R^(3d) is Cl; and R² is 2-chloro-5-thiazolyl.

Table 4

Table 4 is identical to Table 1, except that R^(3c) is F. For example,the first compound in Table 4 is the compound of Formula T-1 whereinR^(a), R^(b), R^(c), R^(d), R^(e), R^(3a) and R^(3b) are H; R^(3c) is F;R^(3d) is Me; and R² is 2-chloro-5-thiazolyl.

Table 5

Table 5 is identical to Table 1, except that R^(3b) is F. For example,the first compound in Table 5 is the compound of Formula T-1 whereinR^(a), R^(b), R^(c), R^(d), R^(e), R^(3a) and R^(3c) are H; R^(3b) is F;R^(3d) is Me; and R² is 2-chloro-5-thiazolyl.

Table 6

Table 6 is identical to Table 1, except that R^(3a) is F. For example,the first compound in Table 6 is the compound of Formula T-1 whereinR^(a), R^(b), R^(c), R^(d), R^(e), R^(3b) and R^(3c) are H; R^(3a) is F;R^(3d) is Me; and R² is 2-chloro-5-thiazolyl.

Table 7

Table 7 is identical to Table 1, except that R^(3d) is Br. For example,the first compound in Table 7 is the compound of Formula T-1 whereinR^(a), R^(b), R^(c), R^(d), R^(e), R^(3a), R^(3b) and R^(3c) are H;R^(3d) is Br; and R² is 2-chloro-5-thiazolyl.

Table 8

Table 8 is identical to Table 1, except that R² is 6-chloro-3-pyridinyl.For example, the first compound in Table 8 is the compound of FormulaT-1 wherein R^(a), R^(b), R^(c), R^(d), R^(e), R^(3a), R^(3b) and R^(3c)are H; R^(3d) is Me; and R² is 6-chloro-3-pyridinyl.

Table 8a

Table 8a is identical to Table 1, except that R² is 6-bromo-3-pyridinyl.For example, the first compound in Table 8a is the compound of FormulaT-1 wherein R^(a), R^(b), R^(c), R^(d), R^(e), R^(3a), R^(3b) and R^(3c)are H; R^(3d) is Me; and R² is 6-bromo-3-pyridinyl.

Table 8b

Table 8b is identical to Table 1, except that R² is6-methyl-3-pyridinyl. For example, the first compound in Table 8b is thecompound of Formula T-1 wherein R^(a), R^(b), R^(c), R^(d), R^(e),R^(3a), R^(3b) and R^(3c) are H; R^(3d) is Me; and R² is6-methyl-3-pyridinyl.

Table 8c

Table 8c is identical to Table 1, except that R² is 3-pyridinyl. Forexample, the first compound in Table 8c is the compound of Formula T-1wherein R^(a), R^(b), R^(c), R^(d), R^(e), R^(3a), R^(3b) and R^(3c) areH; R^(3d) is Me; and R² is 3-pyridinyl.

Table 9

Table 9 is identical to Table 1, except that R² is 5-thiazolyl. Forexample, the first compound in Table 9 is the compound of Formula T-1wherein R^(a), R^(b), R^(c), R^(d), R^(e), R^(3a), R^(3b) and R^(3c) areH; R^(3d) is Me; and R² is 5-thiazolyl.

Table 10

Table 10 is identical to Table 1, except that R² is2-methyl-5-thiazolyl. For example, the first compound in Table 10 is thecompound of Formula T-1 wherein R^(a), R^(b), R^(c), R^(d), R^(e),R^(3a), R^(3b) and R^(3c) are H; R^(3d) is Me; and R² is2-methyl-5-thiazolyl.

Table 10a

Table 10a is identical to Table 1, except that R² is2-methyl-5-oxazolyl. For example, the first compound in Table 10a is thecompound of Formula T-1 wherein R^(a), R^(b), R^(c), R^(d), R^(e),R^(3a), R^(3b) and R^(3c) are H; R^(3d) is Me; and R² is2-methyl-5-oxazolyl.

Table 11

Table 11 is identical to Table 1, except that R² is6-fluoro-3-pyridinyl. For example, the first compound in Table 11 is thecompound of Formula T-1 wherein R^(a), R^(b), R^(c), R^(d), R^(e),R^(3a), R^(3b) and R^(3c) are H; R^(3d) is Me; and R² is6-fluoro-3-pyridinyl.

Table 12

Table 12 is identical to Table 1, except that R² is 2-bromo-5-thiazolyl.For example, the first compound in Table 12 is the compound of FormulaT-1 wherein R^(a), R^(b), R^(c), R^(d), R^(e), R^(3a), R^(3b) and R^(3c)are H; R^(3d) is Me; and R² is 2-bromo-5-thiazolyl.

Table 12a

Table 12a is identical to Table 1, except that R² is2-fluoro-5-thiazolyl. For example, the first compound in Table 12a isthe compound of Formula T-1 wherein R^(a), R^(b), R^(c), R^(d), R^(e),R^(3a), R^(3b) and R^(3c) are H; R^(3d) is Me; and R² is2-fluoro-5-thiazolyl.

Table 13

Table 13 is identical to Table 1, except that R² is 4-pyrimidinyl. Forexample, the first compound in Table 13 is the compound of Formula T-1wherein R^(a), R^(b), R^(c), R^(d), R^(e), R^(3a), R^(3b) and R^(3c) areH; R^(3d) is Me; and R² is 4-pyrimidinyl.

Table 13a

Table 13a is identical to Table 1, except that R² is2-methyl-4-pyrimidinyl. For example, the first compound in Table 13a isthe compound of Formula T-1 wherein R^(a), R^(b), R^(c), R^(d), R^(e),R^(3a), R^(3b) and R^(3c) are H; R^(3d) is Me; and R² is2-methyl-4-pyrimidinyl.

Table 14

Table 14 is identical to Table 1, except that R² isN-methyl-4-pyrazolyl. For example, the first compound in Table 14 is thecompound of Formula T-1 wherein R^(a), R^(b), R^(c), R^(d), R^(e),R^(3a), R^(3b) and R^(3c) are H; R^(3d) is Me; and R² isN-methyl-4-pyrazolyl.

Table 15

Table 15 is identical to Table 1, except that R² is CF₃. For example,the first compound in Table 15 is the compound of Formula T-1 whereinR^(a), R^(b), R^(c), R^(d), R^(e), R^(3a), R^(3b) and R^(3c) are H;R^(3d) is Me; and R² is CF₃.

Table 16

Table 16 is identical to Table 1, except that R^(3c) and R^(3d) aretaken together to form a phenyl ring. For example, the first compound inTable 16 is the compound shown immediately below wherein R^(a), R^(b),R^(c), R^(d), R^(e), R^(3a) and R^(3b) are H; and R² is2-chloro-5-thiazolyl.

Table 17

Table 17 is identical to Table 1, except that the chemical structureunder the Table 17 heading is replaced with the following structure:

For example, the first compound in Table 17 is the structure shownimmediately above wherein R^(a), R^(b), R^(c), R^(d), R^(e), R^(3a),R^(3b) and R^(3c) are H; R^(3d) is Me; and R² is 2-chloro-5-thiazolyl.

TABLE 17a

R^(a) R R² is 2-chloro-5-thiazolyl; R^(3d) is Me H4-chloro-2-fluorophenyl H 2-fluoro-4-(trifluoromethyl)phenyl H2-chloro-4-(trifluoromethyl)phenyl H 2-fluoro-5-(trifluoromethyl)phenylH 2-fluoro-5-(trifluoromethoxy)phenyl cyano 4-chloro-2-fluorophenylcyano 2-fluoro-4-(trifluoromethyl)phenyl cyano2-chloro-4-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethoxy)phenyl OCH₃ 4-chloro-2-fluorophenyl OCH₃2-fluoro-4-(trifluoromethyl)phenyl F 4-chloro-2-fluorophenyl F2-fluoro-4-(trifluoromethyl)phenyl F 2-chloro-4-(trifluoromethyl)phenylF 2-fluoro-5-(trifluoromethyl)phenyl F2-fluoro-5-(trifluoromethoxy)phenyl CH₃ 4-chloro-2-fluorophenyl CH₃2-fluoro-4-(trifluoromethyl)phenyl CH₃2-chloro-4-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethoxy)phenyl OCH₃2-chloro-4-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethoxy)phenyl R² is 2-chloro-5-thiazolyl; R^(3d)is OMe H 4-chloro-2-fluorophenyl H 2-fluoro-4-(trifluoromethyl)phenyl H2-chloro-4-(trifluoromethyl)phenyl H 2-fluoro-5-(trifluoromethyl)phenylH 2-fluoro-5-(trifluoromethoxy)phenyl cyano 4-chloro-2-fluorophenylcyano 2-fluoro-4-(trifluoromethyl)phenyl cyano2-chloro-4-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethoxy)phenyl OCH₃ 4-chloro-2-fluorophenyl OCH₃2-fluoro-4-(trifluoromethyl)phenyl F 4-chloro-2-fluorophenyl F2-fluoro-4-(trifluoromethyl)phenyl F 2-chloro-4-(trifluoromethyl)phenylF 2-fluoro-5-(trifluoromethyl)phenyl F2-fluoro-5-(trifluoromethoxy)phenyl CH₃ 4-chloro-2-fluorophenyl CH₃2-fluoro-4-(trifluoromethyl)phenyl CH₃2-chloro-4-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethoxy)phenyl OCH₃2-chloro-4-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethoxy)phenyl R² is 2-chloro-5-thiazolyl; R^(3d)is Cl H 4-chloro-2-fluorophenyl H 2-fluoro-4-(trifluoromethyl)phenyl H2-chloro-4-(trifluoromethyl)phenyl H 2-fluoro-5-(trifluoromethyl)phenylH 2-fluoro-5-(trifluoromethoxy)phenyl cyano 4-chloro-2-fluorophenylcyano 2-fluoro-4-(trifluoromethyl)phenyl cyano2-chloro-4-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethoxy)phenyl OCH₃ 4-chloro-2-fluorophenyl OCH₃2-fluoro-4-(trifluoromethyl)phenyl F 4-chloro-2-fluorophenyl F2-fluoro-4-(trifluoromethyl)phenyl F 2-chloro-4-(trifluoromethyl)phenylF 2-fluoro-5-(trifluoromethyl)phenyl F2-fluoro-5-(trifluoromethoxy)phenyl CH₃ 4-chloro-2-fluorophenyl CH₃2-fluoro-4-(trifluoromethyl)phenyl CH₃2-chloro-4-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethoxy)phenyl OCH₃2-chloro-4-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethoxy)phenyl R² is 2-chloro-5-thiazolyl; R^(3d)is Br H 4-chloro-2-fluorophenyl H 2-fluoro-4-(trifluoromethyl)phenyl H2-chloro-4-(trifluoromethyl)phenyl H 2-fluoro-5-(trifluoromethyl)phenylH 2-fluoro-5-(trifluoromethoxy)phenyl cyano 4-chloro-2-fluorophenylcyano 2-fluoro-4-(trifluoromethyl)phenyl cyano2-chloro-4-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethoxy)phenyl OCH₃ 4-chloro-2-fluorophenyl OCH₃2-fluoro-4-(trifluoromethyl)phenyl F 4-chloro-2-fluorophenyl F2-fluoro-4-(trifluoromethyl)phenyl F 2-chloro-4-(trifluoromethyl)phenylF 2-fluoro-5-(trifluoromethyl)phenyl F2-fluoro-5-(trifluoromethoxy)phenyl CH₃ 4-chloro-2-fluorophenyl CH₃2-fluoro-4-(trifluoromethyl)phenyl CH₃2-chloro-4-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethoxy)phenyl OCH₃2-chloro-4-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethoxy)phenyl R² is 2-bromo-5-thiazolyl; R^(3d) isMe H 4-chloro-2-fluorophenyl H 2-fluoro-4-(trifluoromethyl)phenyl H2-chloro-4-(trifluoromethyl)phenyl H 2-fluoro-5-(trifluoromethyl)phenylH 2-fluoro-5-(trifluoromethoxy)phenyl cyano 4-chloro-2-fluorophenylcyano 2-fluoro-4-(trifluoromethyl)phenyl cyano2-chloro-4-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethoxy)phenyl OCH₃ 4-chloro-2-fluorophenyl OCH₃2-fluoro-4-(trifluoromethyl)phenyl F 4-chloro-2-fluorophenyl F2-fluoro-4-(trifluoromethyl)phenyl F 2-chloro-4-(trifluoromethyl)phenylF 2-fluoro-5-(trifluoromethyl)phenyl F2-fluoro-5-(trifluoromethoxy)phenyl CH₃ 4-chloro-2-fluorophenyl CH₃2-fluoro-4-(trifluoromethyl)phenyl CH₃2-chloro-4-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethoxy)phenyl OCH₃2-chloro-4-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethoxy)phenyl R² is 2-fluoro-5-thiazolyl; R^(3d)is Me H 4-chloro-2-fluorophenyl H 2-fluoro-4-(trifluoromethyl)phenyl H2-chloro-4-(trifluoromethyl)phenyl H 2-fluoro-5-(trifluoromethyl)phenylH 2-fluoro-5-(trifluoromethoxy)phenyl cyano 4-chloro-2-fluorophenylcyano 2-fluoro-4-(trifluoromethyl)phenyl cyano2-chloro-4-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethoxy)phenyl OCH₃ 4-chloro-2-fluorophenyl OCH₃2-fluoro-4-(trifluoromethyl)phenyl F 4-chloro-2-fluorophenyl F2-fluoro-4-(trifluoromethyl)phenyl F 2-chloro-4-(trifluoromethyl)phenylF 2-fluoro-5-(trifluoromethyl)phenyl F2-fluoro-5-(trifluoromethoxy)phenyl CH₃ 4-chloro-2-fluorophenyl CH₃2-fluoro-4-(trifluoromethyl)phenyl CH₃2-chloro-4-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethoxy)phenyl OCH₃2-chloro-4-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethoxy)phenyl R² is 5-thiazolyl; R^(3d) is Me H4-chloro-2-fluorophenyl H 2-fluoro-4-(trifluoromethyl)phenyl H2-chloro-4-(trifluoromethyl)phenyl H 2-fluoro-5-(trifluoromethyl)phenylH 2-fluoro-5-(trifluoromethoxy)phenyl cyano 4-chloro-2-fluorophenylcyano 2-fluoro-4-(trifluoromethyl)phenyl cyano2-chloro-4-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethoxy)phenyl OCH₃ 4-chloro-2-fluorophenyl OCH₃2-fluoro-4-(trifluoromethyl)phenyl F 4-chloro-2-fluorophenyl F2-fluoro-4-(trifluoromethyl)phenyl F 2-chloro-4-(trifluoromethyl)phenylF 2-fluoro-5-(trifluoromethyl)phenyl F2-fluoro-5-(trifluoromethoxy)phenyl CH₃ 4-chloro-2-fluorophenyl CH₃2-fluoro-4-(trifluoromethyl)phenyl CH₃2-chloro-4-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethoxy)phenyl OCH₃2-chloro-4-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethoxy)phenyl R² is 2-methyl-5-thiazolyl; R^(3d)is Me H 4-chloro-2-fluorophenyl H 2-fluoro-4-(trifluoromethyl)phenyl H2-chloro-4-(trifluoromethyl)phenyl H 2-fluoro-5-(trifluoromethyl)phenylH 2-fluoro-5-(trifluoromethoxy)phenyl cyano 4-chloro-2-fluorophenylcyano 2-fluoro-4-(trifluoromethyl)phenyl cyano2-chloro-4-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethoxy)phenyl OCH₃ 4-chloro-2-fluorophenyl OCH₃2-fluoro-4-(trifluoromethyl)phenyl F 4-chloro-2-fluorophenyl F2-fluoro-4-(trifluoromethyl)phenyl F 2-chloro-4-(trifluoromethyl)phenylF 2-fluoro-5-(trifluoromethyl)phenyl F2-fluoro-5-(trifluoromethoxy)phenyl CH₃ 4-chloro-2-fluorophenyl CH₃2-fluoro-4-(trifluoromethyl)phenyl CH₃2-chloro-4-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethoxy)phenyl OCH₃2-chloro-4-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethoxy)phenyl R² is 6-chloro-3-pyridinyl; R^(3d)is Me H 4-chloro-2-fluorophenyl H 2-fluoro-4-(trifluoromethyl)phenyl H2-chloro-4-(trifluoromethyl)phenyl H 2-fluoro-5-(trifluoromethyl)phenylH 2-fluoro-5-(trifluoromethoxy)phenyl cyano 4-chloro-2-fluorophenylcyano 2-fluoro-4-(trifluoromethyl)phenyl cyano2-chloro-4-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethoxy)phenyl OCH₃ 4-chloro-2-fluorophenyl OCH₃2-fluoro-4-(trifluoromethyl)phenyl F 4-chloro-2-fluorophenyl F2-fluoro-4-(trifluoromethyl)phenyl F 2-chloro-4-(trifluoromethyl)phenylF 2-fluoro-5-(trifluoromethyl)phenyl F2-fluoro-5-(trifluoromethoxy)phenyl CH₃ 4-chloro-2-fluorophenyl CH₃2-fluoro-4-(trifluoromethyl)phenyl CH₃2-chloro-4-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethoxy)phenyl OCH₃2-chloro-4-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethoxy)phenyl R² is 6-fluoro-3-pyridinyl; R^(3d)is Me H 4-chloro-2-fluorophenyl H 2-fluoro-4-(trifluoromethyl)phenyl H2-chloro-4-(trifluoromethyl)phenyl H 2-fluoro-5-(trifluoromethyl)phenylH 2-fluoro-5-(trifluoromethoxy)phenyl cyano 4-chloro-2-fluorophenylcyano 2-fluoro-4-(trifluoromethyl)phenyl cyano2-chloro-4-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethoxy)phenyl OCH₃ 4-chloro-2-fluorophenyl OCH₃2-fluoro-4-(trifluoromethyl)phenyl F 4-chloro-2-fluorophenyl F2-fluoro-4-(trifluoromethyl)phenyl F 2-chloro-4-(trifluoromethyl)phenylF 2-fluoro-5-(trifluoromethyl)phenyl F2-fluoro-5-(trifluoromethoxy)phenyl CH₃ 4-chloro-2-fluorophenyl CH₃2-fluoro-4-(trifluoromethyl)phenyl CH₃2-chloro-4-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethoxy)phenyl OCH₃2-chloro-4-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethoxy)phenyl R² is 6-bromo-3-pyridinyl; R^(3d) isMe H 4-chloro-2-fluorophenyl H 2-fluoro-4-(trifluoromethyl)phenyl H2-chloro-4-(trifluoromethyl)phenyl H 2-fluoro-5-(trifluoromethyl)phenylH 2-fluoro-5-(trifluoromethoxy)phenyl cyano 4-chloro-2-fluorophenylcyano 2-fluoro-4-(trifluoromethyl)phenyl cyano2-chloro-4-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethoxy)phenyl OCH₃ 4-chloro-2-fluorophenyl OCH₃2-fluoro-4-(trifluoromethyl)phenyl F 4-chloro-2-fluorophenyl F2-fluoro-4-(trifluoromethyl)phenyl F 2-chloro-4-(trifluoromethyl)phenylF 2-fluoro-5-(trifluoromethyl)phenyl F2-fluoro-5-(trifluoromethoxy)phenyl CH₃ 4-chloro-2-fluorophenyl CH₃2-fluoro-4-(trifluoromethyl)phenyl CH₃2-chloro-4-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethoxy)phenyl OCH₃2-chloro-4-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethoxy)phenyl R² is 6-methyl-3-pyridinyl; R^(3d)is Me H 4-chloro-2-fluorophenyl H 2-fluoro-4-(trifluoromethyl)phenyl H2-chloro-4-(trifluoromethyl)phenyl H 2-fluoro-5-(trifluoromethyl)phenylH 2-fluoro-5-(trifluoromethoxy)phenyl cyano 4-chloro-2-fluorophenylcyano 2-fluoro-4-(trifluoromethyl)phenyl cyano2-chloro-4-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethoxy)phenyl OCH₃ 4-chloro-2-fluorophenyl OCH₃2-fluoro-4-(trifluoromethyl)phenyl F 4-chloro-2-fluorophenyl F2-fluoro-4-(trifluoromethyl)phenyl F 2-chloro-4-(trifluoromethyl)phenylF 2-fluoro-5-(trifluoromethyl)phenyl F2-fluoro-5-(trifluoromethoxy)phenyl CH₃ 4-chloro-2-fluorophenyl CH₃2-fluoro-4-(trifluoromethyl)phenyl CH₃2-chloro-4-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethoxy)phenyl OCH₃2-chloro-4-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethoxy)phenyl R² is 3-pyridinyl; R^(3d) is Me H4-chloro-2-fluorophenyl H 2-fluoro-4-(trifluoromethyl)phenyl H2-chloro-4-(trifluoromethyl)phenyl H 2-fluoro-5-(trifluoromethyl)phenylH 2-fluoro-5-(trifluoromethoxy)phenyl cyano 4-chloro-2-fluorophenylcyano 2-fluoro-4-(trifluoromethyl)phenyl cyano2-chloro-4-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethoxy)phenyl OCH₃ 4-chloro-2-fluorophenyl OCH₃2-fluoro-4-(trifluoromethyl)phenyl F 4-chloro-2-fluorophenyl F2-fluoro-4-(trifluoromethyl)phenyl F 2-chloro-4-(trifluoromethyl)phenylF 2-fluoro-5-(trifluoromethyl)phenyl F2-fluoro-5-(trifluoromethoxy)phenyl CH₃ 4-chloro-2-fluorophenyl CH₃2-fluoro-4-(trifluoromethyl)phenyl CH₃2-chloro-4-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethoxy)phenyl OCH₃2-chloro-4-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethoxy)phenyl R² is 4-pyrimidinyl; R^(3d) is Me H4-chloro-2-fluorophenyl H 2-fluoro-4-(trifluoromethyl)phenyl H2-chloro-4-(trifluoromethyl)phenyl H 2-fluoro-5-(trifluoromethyl)phenylH 2-fluoro-5-(trifluoromethoxy)phenyl cyano 4-chloro-2-fluorophenylcyano 2-fluoro-4-(trifluoromethyl)phenyl cyano2-chloro-4-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethoxy)phenyl OCH₃ 4-chloro-2-fluorophenyl OCH₃2-fluoro-4-(trifluoromethyl)phenyl F 4-chloro-2-fluorophenyl F2-fluoro-4-(trifluoromethyl)phenyl F 2-chloro-4-(trifluoromethyl)phenylF 2-fluoro-5-(trifluoromethyl)phenyl F2-fluoro-5-(trifluoromethoxy)phenyl CH₃ 4-chloro-2-fluorophenyl CH₃2-fluoro-4-(trifluoromethyl)phenyl CH₃2-chloro-4-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethoxy)phenyl OCH₃2-chloro-4-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethoxy)phenyl R² is 2-methyl-4-pyrimidinyl; R^(3d)is Me H 4-chloro-2-fluorophenyl H 2-fluoro-4-(trifluoromethyl)phenyl H2-chloro-4-(trifluoromethyl)phenyl H 2-fluoro-5-(trifluoromethyl)phenylH 2-fluoro-5-(trifluoromethoxy)phenyl cyano 4-chloro-2-fluorophenylcyano 2-fluoro-4-(trifluoromethyl)phenyl cyano2-chloro-4-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethoxy)phenyl OCH₃ 4-chloro-2-fluorophenyl OCH₃2-fluoro-4-(trifluoromethyl)phenyl F 4-chloro-2-fluorophenyl F2-fluoro-4-(trifluoromethyl)phenyl F 2-chloro-4-(trifluoromethyl)phenylF 2-fluoro-5-(trifluoromethyl)phenyl F2-fluoro-5-(trifluoromethoxy)phenyl CH₃ 4-chloro-2-fluorophenyl CH₃2-fluoro-4-(trifluoromethyl)phenyl CH₃2-chloro-4-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethoxy)phenyl OCH₃2-chloro-4-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethoxy)phenyl R² is N-methyl-4-pyrazolyl; R^(3d)is Me H 4-chloro-2-fluorophenyl H 2-fluoro-4-(trifluoromethyl)phenyl H2-chloro-4-(trifluoromethyl)phenyl H 2-fluoro-5-(trifluoromethyl)phenylH 2-fluoro-5-(trifluoromethoxy)phenyl cyano 4-chloro-2-fluorophenylcyano 2-fluoro-4-(trifluoromethyl)phenyl cyano2-chloro-4-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethoxy)phenyl OCH₃ 4-chloro-2-fluorophenyl OCH₃2-fluoro-4-(trifluoromethyl)phenyl F 4-chloro-2-fluorophenyl F2-fluoro-4-(trifluoromethyl)phenyl F 2-chloro-4-(trifluoromethyl)phenylF 2-fluoro-5-(trifluoromethyl)phenyl F2-fluoro-5-(trifluoromethoxy)phenyl CH₃ 4-chloro-2-fluorophenyl CH₃2-fluoro-4-(trifluoromethyl)phenyl CH₃2-chloro-4-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethoxy)phenyl OCH₃2-chloro-4-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethoxy)phenyl R² is CF₃; R^(3d) is Me H4-chloro-2-fluorophenyl H 2-fluoro-4-(trifluoromethyl)phenyl H2-chloro-4-(trifluoromethyl)phenyl H 2-fluoro-5-(trifluoromethyl)phenylH 2-fluoro-5-(trifluoromethoxy)phenyl cyano 4-chloro-2-fluorophenylcyano 2-fluoro-4-(trifluoromethyl)phenyl cyano2-chloro-4-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethoxy)phenyl OCH₃ 4-chloro-2-fluorophenyl OCH₃2-fluoro-4-(trifluoromethyl)phenyl F 4-chloro-2-fluorophenyl F2-fluoro-4-(trifluoromethyl)phenyl F 2-chloro-4-(trifluoromethyl)phenylF 2-fluoro-5-(trifluoromethyl)phenyl F2-fluoro-5-(trifluoromethoxy)phenyl CH₃ 4-chloro-2-fluorophenyl CH₃2-fluoro-4-(trifluoromethyl)phenyl CH₃2-chloro-4-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethoxy)phenyl OCH₃2-chloro-4-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethoxy)phenyl R² is CH₂CF₃; R^(3d) is Me H4-chloro-2-fluorophenyl H 2-fluoro-4-(trifluoromethyl)phenyl H2-chloro-4-(trifluoromethyl)phenyl H 2-fluoro-5-(trifluoromethyl)phenylH 2-fluoro-5-(trifluoromethoxy)phenyl cyano 4-chloro-2-fluorophenylcyano 2-fluoro-4-(trifluoromethyl)phenyl cyano2-chloro-4-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethoxy)phenyl OCH₃ 4-chloro-2-fluorophenyl OCH₃2-fluoro-4-(trifluoromethyl)phenyl F 4-chloro-2-fluorophenyl F2-fluoro-4-(trifluoromethyl)phenyl F 2-chloro-4-(trifluoromethyl)phenylF 2-fluoro-5-(trifluoromethyl)phenyl F2-fluoro-5-(trifluoromethoxy)phenyl CH₃ 4-chloro-2-fluorophenyl CH₃2-fluoro-4-(trifluoromethyl)phenyl CH₃2-chloro-4-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethoxy)phenyl OCH₃2-chloro-4-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethoxy)phenyl R² is CH₂CFClCHF₂; R^(3d) is Me H4-chloro-2-fluorophenyl H 2-fluoro-4-(trifluoromethyl)phenyl H2-chloro-4-(trifluoromethyl)phenyl H 2-fluoro-5-(trifluoromethyl)phenylH 2-fluoro-5-(trifluoromethoxy)phenyl cyano 4-chloro-2-fluorophenylcyano 2-fluoro-4-(trifluoromethyl)phenyl cyano2-chloro-4-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethoxy)phenyl OCH₃ 4-chloro-2-fluorophenyl OCH₃2-fluoro-4-(trifluoromethyl)phenyl F 4-chloro-2-fluorophenyl F2-fluoro-4-(trifluoromethyl)phenyl F 2-chloro-4-(trifluoromethyl)phenylF 2-fluoro-5-(trifluoromethyl)phenyl F2-fluoro-5-(trifluoromethoxy)phenyl CH₃ 4-chloro-2-fluorophenyl CH₃2-fluoro-4-(trifluoromethyl)phenyl CH₃2-chloro-4-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethoxy)phenyl OCH₃2-chloro-4-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethoxy)phenyl

TABLE 17b

R^(a) R R² is 2-chloro-5-thiazolyl; R^(3d) is Me H4-chloro-2-fluorophenyl H 2-fluoro-4-(trifluoromethyl)phenyl H2-chloro-4-(trifluoromethyl)phenyl H 2-fluoro-5-(trifluoromethyl)phenylH 2-fluoro-5-(trifluoromethoxy)phenyl cyano 4-chloro-2-fluorophenylcyano 2-fluoro-4-(trifluoromethyl)phenyl cyano2-chloro-4-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethoxy)phenyl OCH₃ 4-chloro-2-fluorophenyl OCH₃2-fluoro-4-(trifluoromethyl)phenyl F 4-chloro-2-fluorophenyl F2-fluoro-4-(trifluoromethyl)phenyl F 2-chloro-4-(trifluoromethyl)phenylF 2-fluoro-5-(trifluoromethyl)phenyl F2-fluoro-5-(trifluoromethoxy)phenyl CH₃ 4-chloro-2-fluorophenyl CH₃2-fluoro-4-(trifluoromethyl)phenyl CH₃2-chloro-4-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethoxy)phenyl OCH₃2-chloro-4-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethoxy)phenyl R² is 2-chloro-5-thiazolyl; R^(3d)is OMe H 4-chloro-2-fluorophenyl H 2-fluoro-4-(trifluoromethyl)phenyl H2-chloro-4-(trifluoromethyl)phenyl H 2-fluoro-5-(trifluoromethyl)phenylH 2-fluoro-5-(trifluoromethoxy)phenyl cyano 4-chloro-2-fluorophenylcyano 2-fluoro-4-(trifluoromethyl)phenyl cyano2-chloro-4-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethoxy)phenyl OCH₃ 4-chloro-2-fluorophenyl OCH₃2-fluoro-4-(trifluoromethyl)phenyl F 4-chloro-2-fluorophenyl F2-fluoro-4-(trifluoromethyl)phenyl F 2-chloro-4-(trifluoromethyl)phenylF 2-fluoro-5-(trifluoromethyl)phenyl F2-fluoro-5-(trifluoromethoxy)phenyl CH₃ 4-chloro-2-fluorophenyl CH₃2-fluoro-4-(trifluoromethyl)phenyl CH₃2-chloro-4-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethoxy)phenyl OCH₃2-chloro-4-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethoxy)phenyl R² is 2-chloro-5-thiazolyl; R^(3d)is Cl H 4-chloro-2-fluorophenyl H 2-fluoro-4-(trifluoromethyl)phenyl H2-chloro-4-(trifluoromethyl)phenyl H 2-fluoro-5-(trifluoromethyl)phenylH 2-fluoro-5-(trifluoromethoxy)phenyl cyano 4-chloro-2-fluorophenylcyano 2-fluoro-4-(trifluoromethyl)phenyl cyano2-chloro-4-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethoxy)phenyl OCH₃ 4-chloro-2-fluorophenyl OCH₃2-fluoro-4-(trifluoromethyl)phenyl F 4-chloro-2-fluorophenyl F2-fluoro-4-(trifluoromethyl)phenyl F 2-chloro-4-(trifluoromethyl)phenylF 2-fluoro-5-(trifluoromethyl)phenyl F2-fluoro-5-(trifluoromethoxy)phenyl CH₃ 4-chloro-2-fluorophenyl CH₃2-fluoro-4-(trifluoromethyl)phenyl CH₃2-chloro-4-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethoxy)phenyl OCH₃2-chloro-4-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethoxy)phenyl R² is 2-chloro-5-thiazolyl; R^(3d)is Br H 4-chloro-2-fluorophenyl H 2-fluoro-4-(trifluoromethyl)phenyl H2-chloro-4-(trifluoromethyl)phenyl H 2-fluoro-5-(trifluoromethyl)phenylH 2-fluoro-5-(trifluoromethoxy)phenyl cyano 4-chloro-2-fluorophenylcyano 2-fluoro-4-(trifluoromethyl)phenyl cyano2-chloro-4-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethoxy)phenyl OCH₃ 4-chloro-2-fluorophenyl OCH₃2-fluoro-4-(trifluoromethyl)phenyl F 4-chloro-2-fluorophenyl F2-fluoro-4-(trifluoromethyl)phenyl F 2-chloro-4-(trifluoromethyl)phenylF 2-fluoro-5-(trifluoromethyl)phenyl F2-fluoro-5-(trifluoromethoxy)phenyl CH₃ 4-chloro-2-fluorophenyl CH₃2-fluoro-4-(trifluoromethyl)phenyl CH₃2-chloro-4-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethoxy)phenyl OCH₃2-chloro-4-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethoxy)phenyl R² is 2-bromo-5-thiazolyl; R^(3d) isMe H 4-chloro-2-fluorophenyl H 2-fluoro-4-(trifluoromethyl)phenyl H2-chloro-4-(trifluoromethyl)phenyl H 2-fluoro-5-(trifluoromethyl)phenylH 2-fluoro-5-(trifluoromethoxy)phenyl cyano 4-chloro-2-fluorophenylcyano 2-fluoro-4-(trifluoromethyl)phenyl cyano2-chloro-4-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethoxy)phenyl OCH₃ 4-chloro-2-fluorophenyl OCH₃2-fluoro-4-(trifluoromethyl)phenyl F 4-chloro-2-fluorophenyl F2-fluoro-4-(trifluoromethyl)phenyl F 2-chloro-4-(trifluoromethyl)phenylF 2-fluoro-5-(trifluoromethyl)phenyl F2-fluoro-5-(trifluoromethoxy)phenyl CH₃ 4-chloro-2-fluorophenyl CH₃2-fluoro-4-(trifluoromethyl)phenyl CH₃2-chloro-4-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethoxy)phenyl OCH₃2-chloro-4-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethoxy)phenyl R² is 2-fluoro-5-thiazolyl; R^(3d)is Me H 4-chloro-2-fluorophenyl H 2-fluoro-4-(trifluoromethyl)phenyl H2-chloro-4-(trifluoromethyl)phenyl H 2-fluoro-5-(trifluoromethyl)phenylH 2-fluoro-5-(trifluoromethoxy)phenyl cyano 4-chloro-2-fluorophenylcyano 2-fluoro-4-(trifluoromethyl)phenyl cyano2-chloro-4-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethoxy)phenyl OCH₃ 4-chloro-2-fluorophenyl OCH₃2-fluoro-4-(trifluoromethyl)phenyl F 4-chloro-2-fluorophenyl F2-fluoro-4-(trifluoromethyl)phenyl F 2-chloro-4-(trifluoromethyl)phenylF 2-fluoro-5-(trifluoromethyl)phenyl F2-fluoro-5-(trifluoromethoxy)phenyl CH₃ 4-chloro-2-fluorophenyl CH₃2-fluoro-4-(trifluoromethyl)phenyl CH₃2-chloro-4-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethoxy)phenyl OCH₃2-chloro-4-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethoxy)phenyl R² is 5-thiazolyl; R^(3d) is Me H4-chloro-2-fluorophenyl H 2-fluoro-4-(trifluoromethyl)phenyl H2-chloro-4-(trifluoromethyl)phenyl H 2-fluoro-5-(trifluoromethyl)phenylH 2-fluoro-5-(trifluoromethoxy)phenyl cyano 4-chloro-2-fluorophenylcyano 2-fluoro-4-(trifluoromethyl)phenyl cyano2-chloro-4-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethoxy)phenyl OCH₃ 4-chloro-2-fluorophenyl OCH₃2-fluoro-4-(trifluoromethyl)phenyl F 4-chloro-2-fluorophenyl F2-fluoro-4-(trifluoromethyl)phenyl F 2-chloro-4-(trifluoromethyl)phenylF 2-fluoro-5-(trifluoromethyl)phenyl F2-fluoro-5-(trifluoromethoxy)phenyl CH₃ 4-chloro-2-fluorophenyl CH₃2-fluoro-4-(trifluoromethyl)phenyl CH₃2-chloro-4-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethoxy)phenyl OCH₃2-chloro-4-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethoxy)phenyl R² is 2-methyl-5-thiazolyl; R^(3d)is Me H 4-chloro-2-fluorophenyl H 2-fluoro-4-(trifluoromethyl)phenyl H2-chloro-4-(trifluoromethyl)phenyl H 2-fluoro-5-(trifluoromethyl)phenylH 2-fluoro-5-(trifluoromethoxy)phenyl cyano 4-chloro-2-fluorophenylcyano 2-fluoro-4-(trifluoromethyl)phenyl cyano2-chloro-4-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethoxy)phenyl OCH₃ 4-chloro-2-fluorophenyl OCH₃2-fluoro-4-(trifluoromethyl)phenyl F 4-chloro-2-fluorophenyl F2-fluoro-4-(trifluoromethyl)phenyl F 2-chloro-4-(trifluoromethyl)phenylF 2-fluoro-5-(trifluoromethyl)phenyl F2-fluoro-5-(trifluoromethoxy)phenyl CH₃ 4-chloro-2-fluorophenyl CH₃2-fluoro-4-(trifluoromethyl)phenyl CH₃2-chloro-4-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethoxy)phenyl OCH₃2-chloro-4-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethoxy)phenyl R² is 6-chloro-3-pyridinyl; R^(3d)is Me H 4-chloro-2-fluorophenyl H 2-fluoro-4-(trifluoromethyl)phenyl H2-chloro-4-(trifluoromethyl)phenyl H 2-fluoro-5-(trifluoromethyl)phenylH 2-fluoro-5-(trifluoromethoxy)phenyl cyano 4-chloro-2-fluorophenylcyano 2-fluoro-4-(trifluoromethyl)phenyl cyano2-chloro-4-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethoxy)pheny OCH₃ 4-chloro-2-fluorophenyl OCH₃2-fluoro-4-(trifluoromethyl)phenyl F 4-chloro-2-fluorophenyl F2-fluoro-4-(trifluoromethyl)phenyl F 2-chloro-4-(trifluoromethyl)phenylF 2-fluoro-5-(trifluoromethyl)phenyl F2-fluoro-5-(trifluoromethoxy)phenyl CH₃ 4-chloro-2-fluorophenyl CH₃2-fluoro-4-(trifluoromethyl)phenyl CH₃2-chloro-4-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethoxy)phenyl OCH₃2-chloro-4-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethoxy)phenyl R² is 6-fluoro-3-pyridinyl; R^(3d)is Me H 4-chloro-2-fluorophenyl H 2-fluoro-4-(trifluoromethyl)phenyl H2-chloro-4-(trifluoromethyl)phenyl H 2-fluoro-5-(trifluoromethyl)phenylH 2-fluoro-5-(trifluoromethoxy)phenyl cyano 4-chloro-2-fluorophenylcyano 2-fluoro-4-(trifluoromethyl)phenyl cyano2-chloro-4-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethoxy)phenyl OCH₃ 4-chloro-2-fluorophenyl OCH₃2-fluoro-4-(trifluoromethyl)phenyl F 4-chloro-2-fluorophenyl F2-fluoro-4-(trifluoromethyl)phenyl F 2-chloro-4-(trifluoromethyl)phenylF 2-fluoro-5-(trifluoromethyl)phenyl F2-fluoro-5-(trifluoromethoxy)phenyl CH₃ 4-chloro-2-fluorophenyl CH₃2-fluoro-4-(trifluoromethyl)phenyl CH₃2-chloro-4-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethoxy)phenyl OCH₃2-chloro-4-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethoxy)phenyl R² is 6-bromo-3-pyridinyl; R^(3d) isMe H 4-chloro-2-fluorophenyl H 2-fluoro-4-(trifluoromethyl)phenyl H2-chloro-4-(trifluoromethyl)phenyl H 2-fluoro-5-(trifluoromethyl)phenylH 2-fluoro-5-(trifluoromethoxy)phenyl cyano 4-chloro-2-fluorophenylcyano 2-fluoro-4-(trifluoromethyl)phenyl cyano2-chloro-4-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethoxy)phenyl OCH₃ 4-chloro-2-fluorophenyl OCH₃2-fluoro-4-(trifluoromethyl)phenyl F 4-chloro-2-fluorophenyl F2-fluoro-4-(trifluoromethyl)phenyl F 2-chloro-4-(trifluoromethyl)phenylF 2-fluoro-5-(trifluoromethyl)phenyl F2-fluoro-5-(trifluoromethoxy)phenyl CH₃ 4-chloro-2-fluorophenyl CH₃2-fluoro-4-(trifluoromethyl)phenyl CH₃2-chloro-4-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethoxy)phenyl OCH₃2-chloro-4-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethoxy)phenyl R² is 6-methyl-3-pyridinyl; R^(3d)is Me H 4-chloro-2-fluorophenyl H 2-fluoro-4-(trifluoromethyl)phenyl H2-chloro-4-(trifluoromethyl)phenyl H 2-fluoro-5-(trifluoromethyl)phenylH 2-fluoro-5-(trifluoromethoxy)phenyl cyano 4-chloro-2-fluorophenylcyano 2-fluoro-4-(trifluoromethyl)phenyl cyano2-chloro-4-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethoxy)phenyl OCH₃ 4-chloro-2-fluorophenyl OCH₃2-fluoro-4-(trifluoromethyl)phenyl F 4-chloro-2-fluorophenyl F2-fluoro-4-(trifluoromethyl)phenyl F 2-chloro-4-(trifluoromethyl)phenylF 2-fluoro-5-(trifluoromethyl)phenyl F2-fluoro-5-(trifluoromethoxy)phenyl CH₃ 4-chloro-2-fluorophenyl CH₃2-fluoro-4-(trifluoromethyl)phenyl CH₃2-chloro-4-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethoxy)phenyl OCH₃2-chloro-4-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethoxy)phenyl R² is 3-pyridinyl; R^(3d) is Me H4-chloro-2-fluorophenyl H 2-fluoro-4-(trifluoromethyl)phenyl H2-chloro-4-(trifluoromethyl)phenyl H 2-fluoro-5-(trifluoromethyl)phenylH 2-fluoro-5-(trifluoromethoxy)phenyl cyano 4-chloro-2-fluorophenylcyano 2-fluoro-4-(trifluoromethyl)phenyl cyano2-chloro-4-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethoxy)phenyl OCH₃ 4-chloro-2-fluorophenyl OCH₃2-fluoro-4-(trifluoromethyl)phenyl F 4-chloro-2-fluorophenyl F2-fluoro-4-(trifluoromethyl)phenyl F 2-chloro-4-(trifluoromethyl)phenylF 2-fluoro-5-(trifluoromethyl)phenyl F2-fluoro-5-(trifluoromethoxy)phenyl CH₃ 4-chloro-2-fluorophenyl CH₃2-fluoro-4-(trifluoromethyl)phenyl CH₃2-chloro-4-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethoxy)phenyl OCH₃2-chloro-4-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethoxy)phenyl R² is 4-pyrimidinyl; R^(3d) is Me H4-chloro-2-fluorophenyl H 2-fluoro-4-(trifluoromethyl)phenyl H2-chloro-4-(trifluoromethyl)phenyl H 2-fluoro-5-(trifluoromethyl)phenylH 2-fluoro-5-(trifluoromethoxy)phenyl cyano 4-chloro-2-fluorophenylcyano 2-fluoro-4-(trifluoromethyl)phenyl cyano2-chloro-4-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethoxy)phenyl OCH₃ 4-chloro-2-fluorophenyl OCH₃2-fluoro-4-(trifluoromethyl)phenyl F 4-chloro-2-fluorophenyl F2-fluoro-4-(trifluoromethyl)phenyl F 2-chloro-4-(trifluoromethyl)phenylF 2-fluoro-5-(trifluoromethyl)phenyl F2-fluoro-5-(trifluoromethoxy)phenyl CH₃ 4-chloro-2-fluorophenyl CH₃2-fluoro-4-(trifluoromethyl)phenyl CH₃2-chloro-4-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethoxy)phenyl OCH₃2-chloro-4-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethoxy)phenyl R² is 2-methyl-4-pyrimidinyl; R^(3d)is Me H 4-chloro-2-fluorophenyl H 2-fluoro-4-(trifluoromethyl)phenyl H2-chloro-4-(trifluoromethyl)phenyl H 2-fluoro-5-(trifluoromethyl)phenylH 2-fluoro-5-(trifluoromethoxy)phenyl cyano 4-chloro-2-fluorophenylcyano 2-fluoro-4-(trifluoromethyl)phenyl cyano2-chloro-4-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethoxy)phenyl OCH₃ 4-chloro-2-fluorophenyl OCH₃2-fluoro-4-(trifluoromethyl)phenyl F 4-chloro-2-fluorophenyl F2-fluoro-4-(trifluoromethyl)phenyl F 2-chloro-4-(trifluoromethyl)phenylF 2-fluoro-5-(trifluoromethyl)phenyl F2-fluoro-5-(trifluoromethoxy)phenyl CH₃ 4-chloro-2-fluorophenyl CH₃2-fluoro-4-(trifluoromethyl)phenyl CH₃2-chloro-4-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethoxy)phenyl OCH₃2-chloro-4-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethoxy)phenyl R² is N-methyl-4-pyrazolyl; R^(3d)is Me H 4-chloro-2-fluorophenyl H 2-fluoro-4-(trifluoromethyl)phenyl H2-chloro-4-(trifluoromethyl)phenyl H 2-fluoro-5-(trifluoromethyl)phenylH 2-fluoro-5-(trifluoromethoxy)phenyl cyano 4-chloro-2-fluorophenylcyano 2-fluoro-4-(trifluoromethyl)phenyl cyano2-chloro-4-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethoxy)phenyl OCH₃ 4-chloro-2-fluorophenyl OCH₃2-fluoro-4-(trifluoromethyl)phenyl F 4-chloro-2-fluorophenyl F2-fluoro-4-(trifluoromethyl)phenyl F 2-chloro-4-(trifluoromethyl)phenylF 2-fluoro-5-(trifluoromethyl)phenyl F2-fluoro-5-(trifluoromethoxy)phenyl CH₃ 4-chloro-2-fluorophenyl CH₃2-fluoro-4-(trifluoromethyl)phenyl CH₃2-chloro-4-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethoxy)phenyl OCH₃2-chloro-4-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethoxy)phenyl R² is CF₃; R^(3d) is Me H4-chloro-2-fluorophenyl H 2-fluoro-4-(trifluoromethyl)phenyl H2-chloro-4-(trifluoromethyl)phenyl H 2-fluoro-5-(trifluoromethyl)phenylH 2-fluoro-5-(trifluoromethoxy)phenyl cyano 4-chloro-2-fluorophenylcyano 2-fluoro-4-(trifluoromethyl)phenyl cyano2-chloro-4-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethoxy)phenyl OCH₃ 4-chloro-2-fluorophenyl OCH₃2-fluoro-4-(trifluoromethyl)phenyl F 4-chloro-2-fluorophenyl F2-fluoro-4-(trifluoromethyl)phenyl F 2-chloro-4-(trifluoromethyl)phenylF 2-fluoro-5-(trifluoromethyl)phenyl F2-fluoro-5-(trifluoromethoxy)phenyl CH₃ 4-chloro-2-fluorophenyl CH₃2-fluoro-4-(trifluoromethyl)phenyl CH₃2-chloro-4-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethoxy)phenyl OCH₃2-chloro-4-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethoxy)phenyl R² is CH₂CF₃; R^(3d) is Me H4-chloro-2-fluorophenyl H 2-fluoro-4-(trifluoromethyl)phenyl H2-chloro-4-(trifluoromethyl)phenyl H 2-fluoro-5-(trifluoromethyl)phenylH 2-fluoro-5-(trifluoromethoxy)phenyl cyano 4-chloro-2-fluorophenylcyano 2-fluoro-4-(trifluoromethyl)phenyl cyano2-chloro-4-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethoxy)phenyl OCH₃ 4-chloro-2-fluorophenyl OCH₃2-fluoro-4-(trifluoromethyl)phenyl F 4-chloro-2-fluorophenyl F2-fluoro-4-(trifluoromethyl)phenyl F 2-chloro-4-(trifluoromethyl)phenylF 2-fluoro-5-(trifluoromethyl)phenyl F2-fluoro-5-(trifluoromethoxy)phenyl CH₃ 4-chloro-2-fluorophenyl CH₃2-fluoro-4-(trifluoromethyl)phenyl CH₃2-chloro-4-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethoxy)phenyl OCH₃2-chloro-4-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethoxy)phenyl R² is CH₂CFClCHF₂; R^(3d) is Me H4-chloro-2-fluorophenyl H 2-fluoro-4-(trifluoromethyl)phenyl H2-chloro-4-(trifluoromethyl)phenyl H 2-fluoro-5-(trifluoromethyl)phenylH 2-fluoro-5-(trifluoromethoxy)phenyl cyano 4-chloro-2-fluorophenylcyano 2-fluoro-4-(trifluoromethyl)phenyl cyano2-chloro-4-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethyl)phenyl cyano2-fluoro-5-(trifluoromethoxy)phenyl OCH₃ 4-chloro-2-fluorophenyl OCH₃2-fluoro-4-(trifluoromethyl)phenyl F 4-chloro-2-fluorophenyl F2-fluoro-4-(trifluoromethyl)phenyl F 2-chloro-4-(trifluoromethyl)phenylF 2-fluoro-5-(trifluoromethyl)phenyl F2-fluoro-5-(trifluoromethoxy)phenyl CH₃ 4-chloro-2-fluorophenyl CH₃2-fluoro-4-(trifluoromethyl)phenyl CH₃2-chloro-4-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethyl)phenyl CH₃2-fluoro-5-(trifluoromethoxy)phenyl OCH₃2-chloro-4-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethyl)phenyl OCH₃2-fluoro-5-(trifluoromethoxy)phenyl

TABLE 17c

R R² is 2-chloro-5-thiazolyl; R^(3d) is Me 4-chloro-2-fluorophenyl2-fluoro-4-(trifluoromethyl)phenyl 4-cyano-2-fluorophenyl2-chloro-4-(trifluoromethyl)phenyl 2-fluoro-5-(trifluoromethyl)phenyl2-fluoro-5-(trifluoromethoxy)phenyl 2-chloro-4-cyanophenyl4-chloro-2-methylphenyl R² is 2-chloro-5-thiazolyl; R^(3d) is OMe4-chloro-2-fluorophenyl 2-fluoro-4-(trifluoromethyl)phenyl4-cyano-2-fluorophenyl 2-chloro-4-(trifluoromethyl)phenyl2-fluoro-5-(trifluoromethyl)phenyl 2-fluoro-5-(trifluoromethoxy)phenyl2-chloro-4-cyanophenyl 4-chloro-2-methylphenyl R² is2-chloro-5-thiazolyl; R^(3d) is Cl 4-chloro-2-fluorophenyl2-fluoro-4-(trifluoromethyl)phenyl 4-cyano-2-fluorophenyl2-chloro-4-(trifluoromethyl)phenyl 2-fluoro-5-(trifluoromethyl)2-fluoro-5-(trifluoromethoxy)phenyl 2-chloro-4-cyanophenylphenyl4-chloro-2-methylphenyl R² is 2-chloro-5-thiazolyl; R^(3d) is Br4-chloro-2-fluorophenyl 2-fluoro-4-(trifluoromethyl)phenyl4-cyano-2-fluorophenyl 2-chloro-4-(trifluoromethyl)phenyl2-fluoro-5-(trifluoromethyl)phenyl 2-fluoro-5-(trifluoromethoxy)phenyl2-chloro-4-cyanophenyl 4-chloro-2-methylphenyl R² is2-bromo-5-thiazolyl; R^(3d) is Me 4-chloro-2-fluorophenyl2-fluoro-4-(trifluoromethyl)phenyl 4-cyano-2-fluorophenyl2-chloro-4-(trifluoromethyl)phenyl 2-fluoro-5-(trifluoromethyl)phenyl2-fluoro-5-(trifluoromethoxy)phenyl 2-chloro-4-cyanophenyl4-chloro-2-methylphenyl R² is 2-fluoro-5-thiazolyl; R^(3d) is Me4-chloro-2-fluorophenyl 2-fluoro-4-(trifluoromethyl)phenyl4-cyano-2-fluorophenyl 2-chloro-4-(trifluoromethyl)phenyl2-fluoro-5-(trifluoromethyl)phenyl 2-fluoro-5-(trifluoromethoxy)phenyl2-chloro-4-cyanophenyl 4-chloro-2-methylphenyl R² is 5-thiazolyl; R^(3d)is Me 4-chloro-2-fluorophenyl 2-fluoro-4-(trifluoromethyl)phenyl4-cyano-2-fluorophenyl 2-chloro-4-(trifluoromethyl)phenyl2-fluoro-5-(trifluoromethyl)phenyl 2-fluoro-5-(trifluoromethoxy)phenyl2-chloro-4-cyanophenyl 4-chloro-2-methylphenyl R² is2-methyl-5-thiazolyl; R^(3d) is Me 4-chloro-2-fluorophenyl2-fluoro-4-(trifluoromethyl)phenyl 4-cyano-2-fluorophenyl2-chloro-4-(trifluoromethyl)phenyl 2-fluoro-5-(trifluoromethyl)phenyl2-fluoro-5-(trifluoromethoxy)phenyl 2-chloro-4-cyanophenyl4-chloro-2-methylphenyl R² is 6-chloro-3-pyridinyl; R^(3d) is Me4-chloro-2-fluorophenyl 2-fluoro-4-(trifluoromethyl)phenyl4-cyano-2-fluorophenyl 2-chloro-4-(trifluoromethyl)phenyl2-fluoro-5-(trifluoromethyl)phenyl 2-fluoro-5-(trifluoromethoxy)phenyl2-chloro-4-cyanophenyl 4-chloro-2-methylphenyl R² is6-fluoro-3-pyridinyl; R^(3d) is Me 4-chloro-2-fluorophenyl2-fluoro-4-(trifluoromethyl)phenyl 4-cyano-2-fluorophenyl2-chloro-4-(trifluoromethyl)phenyl 2-fluoro-5-(trifluoromethyl)phenyl2-fluoro-5-(trifluoromethoxy)phenyl 2-chloro-4-cyanophenyl4-chloro-2-methylphenyl R² is 6-bromo-3-pyridinyl; R^(3d) is Me4-chloro-2-fluorophenyl 2-fluoro-4-(trifluoromethyl)phenyl4-cyano-2-fluorophenyl 2-chloro-4-(trifluoromethyl)phenyl2-fluoro-5-(trifluoromethyl)phenyl 2-fluoro-5-(trifluoromethoxy)phenyl2-chloro-4-cyanophenyl 4-chloro-2-methylphenyl R² is6-methyl-3-pyridinyl; R^(3d) is Me 4-chloro-2-fluorophenyl2-fluoro-4-(trifluoromethyl)phenyl 4-cyano-2-fluorophenyl2-chloro-4-(trifluoromethyl)phenyl 2-fluoro-5-(trifluoromethyl)phenyl2-fluoro-5-(trifluoromethoxy)phenyl 2-chloro-4-cyanophenyl4-chloro-2-methylphenyl R² is 3-pyridinyl; R^(3d) is Me4-chloro-2-fluorophenyl 2-fluoro-4-(trifluoromethyl)phenyl4-cyano-2-fluorophenyl 2-chloro-4-(trifluoromethyl)phenyl2-fluoro-5-(trifluoromethyl)phenyl 2-fluoro-5-(trifluoromethoxy)phenyl2-chloro-4-cyanophenyl 4-chloro-2-methylphenyl R² is 4-pyrimidinyl;R^(3d) is Me 4-chloro-2-fluorophenyl 2-fluoro-4-(trifluoromethyl)phenyl4-cyano-2-fluorophenyl 2-chloro-4-(trifluoromethyl)phenyl2-fluoro-5-(trifluoromethyl)phenyl 2-fluoro-5-(trifluoromethoxy)phenyl2-chloro-4-cyanophenyl 4-chloro-2-methylphenyl R² is2-methyl-4-pyrimidinyl; R^(3d) is Me 4-chloro-2-fluorophenyl2-fluoro-4-(trifluoromethyl)phenyl 4-cyano-2-fluorophenyl2-chloro-4-(trifluoromethyl)phenyl 2-fluoro-5-(trifluoromethyl)phenyl2-fluoro-5-(trifluoromethoxy)phenyl 2-chloro-4-cyanophenyl4-chloro-2-methylphenyl R² is N-methyl-4-pyrazolyl; R^(3d) is Me4-chloro-2-fluorophenyl 2-fluoro-4-(trifluoromethyl)phenyl4-cyano-2-fluorophenyl 2-chloro-4-(trifluoromethyl)phenyl2-fluoro-5-(trifluoromethyl)phenyl 2-fluoro-5-(trifluoromethoxy)phenyl2-chloro-4-cyanophenyl 4-chloro-2-methylphenyl R² is CF₃; R^(3d) is Me4-chloro-2-fluorophenyl 2-fluoro-4-(trifluoromethyl)phenyl4-cyano-2-fluorophenyl 2-chloro-4-(trifluoromethyl)phenyl2-fluoro-5-(trifluoromethyl)phenyl 2-fluoro-5-(trifluoromethoxy)phenyl2-chloro-4-cyanophenyl 4-chloro-2-methylphenyl R² is CH₂CF₃; R^(3d) isMe 4-chloro-2-fluorophenyl 2-fluoro-4-(trifluoromethyl)phenyl4-cyano-2-fluorophenyl 2-chloro-4-(trifluoromethyl)phenyl2-fluoro-5-(trifluoromethyl)phenyl 2-fluoro-5-(trifluoromethoxy)phenyl2-chloro-4-cyanophenyl 4-chloro-2-methylphenyl R² is CH₂CFClCHF₂; R^(3d)is Me 4-chloro-2-fluorophenyl 2-fluoro-4-(trifluoromethyl)phenyl4-cyano-2-fluorophenyl 2-chloro-4-(trifluoromethyl)phenyl2-fluoro-5-(trifluoromethyl)phenyl 2-fluoro-5-(trifluoromethoxy)phenyl2-chloro-4-cyanophenyl 4-chloro-2-methylphenyl

TABLE 18

ZR¹ R² is 2-chloro-5-thiazolyl; R^(3d) is Me 4-CF₃-2-pyridinyl2-Cl-4-pyridinyl 2-F-4-pyridinyl 2-Br-4-pyridinyl 2-CN-4-pyridinyl2-CF₃-4-pyridinyl 2-OCF₃-4-pyridinyl 2-OCH₃-4-pyridinyl6-OCH₃-2-pyridinyl 6-CF₃-2-pyridinyl 6-OCF₃-2-pyridinyl4-OCF₃-2-pyridinyl 4-CH₃-2-pyridinyl 4-OCH₃-2-pyridinyl 4-CN-2-pyridinyl4-Cl-2-pyridinyl 6-CH₃-2-pyridinyl 6-CN-2-pyridinyl 6-Cl-2-pyridinyl R²is 2-chloro-5-thiazolyl; R^(3d) is OMe 4-CF₃-2-pyridinyl2-Cl-4-pyridinyl 2-F-4-pyridinyl 2-Br-4-pyridinyl 2-CN-4-pyridinyl2-CF₃-4-pyridinyl 2-OCF₃-4-pyridinyl 2-OCH₃-4-pyridinyl6-OCH₃-2-pyridinyl 6-CF₃-2-pyridinyl 6-OCF₃-2-pyridinyl4-OCF₃-2-pyridinyl 4-CH₃-2-pyridinyl 4-OCH₃-2-pyridinyl 4-CN-2-pyridinyl4-Cl-2-pyridinyl 6-CH₃-2-pyridinyl 6-CN-2-pyridinyl 6-Cl-2-pyridinyl R²is 2-chloro-5-thiazolyl; R^(3d) is Cl 4-CF₃-2-pyridinyl 2-Cl-4-pyridinyl2-F-4-pyridinyl 2-Br-4-pyridinyl 2-CN-4-pyridinyl 2-CF₃-4-pyridinyl2-OCF₃-4-pyridinyl 2-OCH₃-4-pyridinyl 6-OCH₃-2-pyridinyl6-CF₃-2-pyridinyl 6-OCF₃-2-pyridinyl 4-OCF₃-2-pyridinyl4-CH₃-2-pyridinyl 4-OCH₃-2-pyridinyl 4-CN-2-pyridinyl 4-Cl-2-pyridinyl6-CH₃-2-pyridinyl 6-CN-2-pyridinyl 6-Cl-2-pyridinyl R² is2-chloro-5-thiazolyl; R^(3d) is Br 4-CF₃-2-pyridinyl 2-Cl-4-pyridinyl2-F-4-pyridinyl 2-Br-4-pyridinyl 2-CN-4-pyridinyl 2-CF₃-4-pyridinyl2-OCF₃-4-pyridinyl 2-OCH₃-4-pyridinyl 6-OCH₃-2-pyridinyl6-CF₃-2-pyridinyl 6-OCF₃-2-pyridinyl 4-OCF₃-2-pyridinyl4-CH₃-2-pyridinyl 4-OCH₃-2-pyridinyl 4-CN-2-pyridinyl 4-Cl-2-pyridinyl6-CH₃-2-pyridinyl 6-CN-2-pyridinyl 6-Cl-2-pyridinyl R² is2-bromo-5-thiazolyl; R^(3d) is Me 4-CF₃-2-pyridinyl 2-Cl-4-pyridinyl2-F-4-pyridinyl 2-Br-4-pyridinyl 2-CN-4-pyridinyl 2-CF₃-4-pyridinyl2-OCF₃-4-pyridinyl 2-OCH₃-4-pyridinyl 6-OCH₃-2-pyridinyl6-CF₃-2-pyridinyl 6-OCF₃-2-pyridinyl 4-OCF₃-2-pyridinyl4-CH₃-2-pyridinyl 4-OCH₃-2-pyridinyl 4-CN-2-pyridinyl 4-Cl-2-pyridinyl6-CH₃-2-pyridinyl 6-CN-2-pyridinyl 6-Cl-2-pyridinyl R² is2-fluoro-5-thiaolyl; R^(3d) is Me 4-CF₃-2-pyridinyl 2-Cl-4-pyridinyl2-F-4-pyridinyl 2-Br-4-pyridinyl 2-CN-4-pyridinyl 2-CF₃-4-pyridinyl2-OCF₃-4-pyridinyl 2-OCH₃-4-pyridinyl 6-OCH₃-2-pyridinyl6-CF₃-2-pyridinyl 6-OCF₃-2-pyridinyl 4-OCF₃-2-pyridinyl4-CH₃-2-pyridinyl 4-OCH₃-2-pyridinyl 4-CN-2-pyridinyl 4-Cl-2-pyridinyl6-CH₃-2-pyridinyl 6-CN-2-pyridinyl 6-Cl-2-pyridinyl R² is 5-thiazolyl;R^(3d) is Me 4-CF₃-2-pyridinyl 2-Cl-4-pyridinyl 2-F-4-pyridinyl2-Br-4-pyridinyl 2-CN-4-pyridinyl 2-CF₃-4-pyridinyl 2-OCF₃-4-pyridinyl2-OCH₃-4-pyridinyl 6-OCH₃-2-pyridinyl 6-CF₃-2-pyridinyl6-OCF₃-2-pyridinyl 4-OCF₃-2-pyridinyl 4-CH₃-2-pyridinyl4-OCH₃-2-pyridinyl 4-CN-2-pyridinyl 4-Cl-2-pyridinyl 6-CH₃-2-pyridinyl6-CN-2-pyridinyl 6-Cl-2-pyridinyl R² is 2-methyl-5-thiazolyl; R^(3d) isMe 4-CF₃-2-pyridinyl 2-Cl-4-pyridinyl 2-F-4-pyridinyl 2-Br-4-pyridinyl2-CN-4-pyridinyl 2-CF₃-4-pyridinyl 2-OCF₃-4-pyridinyl 2-OCH₃-4-pyridinyl6-OCH₃-2-pyridinyl 6-CF₃-2-pyridinyl 6-OCF₃-2-pyridinyl4-OCF₃-2-pyridinyl 4-CH₃-2-pyridinyl 4-OCH₃-2-pyridinyl 4-CN-2-pyridinyl4-Cl-2-pyridinyl 6-CH₃-2-pyridinyl 6-CN-2-pyridinyl 6-Cl-2-pyridinyl R²is 6-chloro-3-pyridinyl; R^(3d) is Me 4-CF₃-2-pyridinyl 2-Cl-4-pyridinyl2-F-4-pyridinyl 2-Br-4-pyridinyl 2-CN-4-pyridinyl 2-CF₃-4-pyridinyl2-OCF₃-4-pyridinyl 2-OCH₃-4-pyridinyl 6-OCH₃-2-pyridinyl6-CF₃-2-pyridinyl 6-OCF₃-2-pyridinyl 4-OCF₃-2-pyridinyl4-CH₃-2-pyridinyl 4-OCH₃-2-pyridinyl 4-CN-2-pyridinyl 4-Cl-2-pyridinyl6-CH₃-2-pyridinyl 6-CN-2-pyridinyl 6-Cl-2-pyridinyl R² is6-fluoro-3-pyridinyl; R^(3d) is Me 4-CF₃-2-pyridinyl 2-Cl-4-pyridinyl2-F-4-pyridinyl 2-Br-4-pyridinyl 2-CN-4-pyridinyl 2-CF₃-4-pyridinyl2-OCF₃-4-pyridinyl 2-OCH₃-4-pyridinyl 6-OCH₃-2-pyridinyl6-CF₃-2-pyridinyl 6-OCF₃-2-pyridinyl 4-OCF₃-2-pyridinyl4-CH₃-2-pyridinyl 4-OCH₃-2-pyridinyl 4-CN-2-pyridinyl 4-Cl-2-pyridinyl6-CH₃-2-pyridinyl 6-CN-2-pyridinyl 6-Cl-2-pyridinyl R² is6-bromo-3-pyrdinyl; R^(3d) is Me 4-CF₃-2-pyridinyl 2-Cl-4-pyridinyl2-F-4-pyridinyl 2-Br-4-pyridinyl 2-CN-4-pyridinyl 2-CF₃-4-pyridinyl2-OCF₃-4-pyridinyl 2-OCH₃-4-pyridinyl 6-OCH₃-2-pyridinyl6-CF₃-2-pyridinyl 6-OCF₃-2-pyridinyl 4-OCF₃-2-pyridinyl4-CH₃-2-pyridinyl 4-OCH₃-2-pyridinyl 4-CN-2-pyridinyl 4-Cl-2-pyridinyl6-CH₃-2-pyridinyl 6-CN-2-pyridinyl 6-Cl-2-pyridinyl R² is6-methyl-3-pyridinyl; R^(3d) is Me 4-CF₃-2-pyridinyl 2-Cl-4-pyridinyl2-F-4-pyridinyl 2-Br-4-pyridinyl 2-CN-4-pyridinyl 2-CF₃-4-pyridinyl2-OCF₃-4-pyridinyl 2-OCH₃-4-pyridinyl 6-OCH₃-2-pyridinyl6-CF₃-2-pyridinyl 6-OCF₃-2-pyridinyl 4-OCF₃-2-pyridinyl4-CH₃-2-pyridinyl 4-OCH₃-2-pyridinyl 4-CN-2-pyridinyl 4-Cl-2-pyridinyl6-CH₃-2-pyridinyl 6-CN-2-pyridinyl 6-Cl-2-pyridinyl R² is 3-pyridinyl;R^(3d) is Me 4-CF₃-2-pyridinyl 2-Cl-4-pyridinyl 2-F-4-pyridinyl2-Br-4-pyridinyl 2-CN-4-pyridinyl 2-CF₃-4-pyridinyl 2-OCF₃-4-pyridinyl2-OCH₃-4-pyridinyl 6-OCH₃-2-pyridinyl 6-CF₃-2-pyridinyl6-OCF₃-2-pyridinyl 4-OCF₃-2-pyridinyl 4-CH₃-2-pyridinyl4-OCH₃-2-pyridinyl 4-CN-2-pyridinyl 4-Cl-2-pyridinyl 6-CH₃-2-pyridinyl6-CN-2-pyridinyl 6-Cl-2-pyridinyl R² is 4-pyrimidinyl; R^(3d) is Me4-CF₃-2-pyridinyl 2-Cl-4-pyridinyl 2-F-4-pyridinyl 2-Br-4-pyridinyl2-CN-4-pyridinyl 2-CF₃-4-pyridinyl 2-OCF₃-4-pyridinyl 2-OCH₃-4-pyridinyl6-OCH₃-2-pyridinyl 6-CF₃-2-pyridinyl 6-OCF₃-2-pyridinyl4-OCF₃-2-pyridinyl 4-CH₃-2-pyridinyl 4-OCH₃-2-pyridinyl 4-CN-2-pyridinyl4-Cl-2-pyridinyl 6-CH₃-2-pyridinyl 6-CN-2-pyridinyl 6-Cl-2-pyridinyl R²is 2-methyl-4-pyrimidinyl; R^(3d) is Me 4-CF₃-2-pyridinyl2-Cl-4-pyridinyl 2-F-4-pyridinyl 2-Br-4-pyridinyl 2-CN-4-pyridinyl2-CF₃-4-pyridinyl 2-OCF₃-4-pyridinyl 2-OCH₃-4-pyridinyl6-OCH₃-2-pyridinyl 6-CF₃-2-pyridinyl 6-OCF₃-2-pyridinyl4-OCF₃-2-pyridinyl 4-CH₃-2-pyridinyl 4-OCH₃-2-pyridinyl 4-CN-2-pyridinyl4-Cl-2-pyridinyl 6-CH₃-2-pyridinyl 6-CN-2-pyridinyl 6-Cl-2-pyridinyl R²is N-methyl-4-pyrazolyl; R^(3d) is Me 4-CF₃-2-pyridinyl 2-Cl-4-pyridinyl2-F-4-pyridinyl 2-Br-4-pyridinyl 2-CN-4-pyridinyl 2-CF₃-4-pyridinyl2-OCF₃-4-pyridinyl 2-OCH₃-4-pyridinyl 6-OCH₃-2-pyridinyl6-CF₃-2-pyridinyl 6-OCF₃-2-pyridinyl 4-OCF₃-2-pyridinyl4-CH₃-2-pyridinyl 4-OCH₃-2-pyridinyl 4-CN-2-pyridinyl 4-Cl-2-pyridinyl6-CH₃-2-pyridinyl 6-CN-2-pyridinyl 6-Cl-2-pyridinyl R² is CF₃; R^(3d) isMe 4-CF₃-2-pyridinyl 2-Cl-4-pyridinyl 2-F-4-pyridinyl 2-Br-4-pyridinyl2-CN-4-pyridinyl 2-CF₃-4-pyridinyl 2-OCF₃-4-pyridinyl 2-OCH₃-4-pyridinyl6-OCH₃-2-pyridinyl 6-CF₃-2-pyridinyl 6-OCF₃-2-pyridinyl4-OCF₃-2-pyridinyl 4-CH₃-2-pyridinyl 4-OCH₃-2-pyridinyl 4-CN-2-pyridinyl4-Cl-2-pyridinyl 6-CH₃-2-pyridinyl 6-CN-2-pyridinyl 6-Cl-2-pyridinyl R²is CH₂CF₃; R^(3d) is Me 4-CF₃-2-pyridinyl 2-Cl-4-pyridinyl2-F-4-pyridinyl 2-Br-4-pyridinyl 2-CN-4-pyridinyl 2-CF₃-4-pyridinyl2-OCF₃-4-pyridinyl 2-OCH₃-4-pyridinyl 6-OCH₃-2-pyridinyl6-CF₃-2-pyridinyl 6-OCF₃-2-pyridinyl 4-OCF₃-2-pyridinyl4-CH₃-2-pyridinyl 4-OCH₃-2-pyridinyl 4-CN-2-pyridinyl 4-Cl-2-pyridinyl6-CH₃-2-pyridinyl 6-CN-2-pyridinyl 6-Cl-2-pyridinyl R² is CH₂CFClCHF₂;R^(3d) is Me 4-CF₃-2-pyridinyl 2-Cl-4-pyridinyl 2-F-4-pyridinyl2-Br-4-pyridinyl 2-CN-4-pyridinyl 2-CF₃-4-pyridinyl 2-OCF₃-4-pyridinyl2-OCH₃-4-pyridinyl 6-OCH₃-2-pyridinyl 6-CF₃-2-pyridinyl6-OCF₃-2-pyridinyl 4-OCF₃-2-pyridinyl 4-CH₃-2-pyridinyl4-OCH₃-2-pyridinyl 4-CN-2-pyridinyl 4-Cl-2-pyridinyl 6-CH₃-2-pyridinyl6-CN-2-pyridinyl 6-Cl-2-pyridinyl

TABLE 19

Z-R¹ is phenyl; R^(3b) is H; A is CH═CMe; R⁴ and R⁵ are H; a is 1; R² is2-chloro-5-thiazolyl R^(3a) H Cl Br cyano CHO C(O)Me CO₂Et C(O)NMe₂ MeEt i-Pr c-Pr OMe OEt OCF₃ SMe CH═CH₂ C≡CH CF₃ Ph OPh NMe₂ NHCHO3-F-2-pyridinyl 4-Me-3-pyridinyl 2-cyano-4-pyridinyl Z-R¹ is phenyl;R^(3a) is H; A is CH═CMe; R⁴ and R⁵ are H; a is 1; R² is2-chloro-5-thiazolyl R^(3b) Cl Br cyano Ph CHO C(O)Me CO₂Et C(O)NMe₂ MeEt i-Pr c-Pr OMe OEt OCF₃ SMe CH═CH₂ C≡CH CF₃ OPh NMe₂ NHCHO3-F-2-pyridinyl 4-Me-3-pyridinyl 2-cyano-4-pyridinyl Z-R¹ is phenyl;R^(3a) and R^(3b) are H; A is C(R^(3c))═CH; R⁴ and R⁵ are H; a is 1; R²is 2-chloro-5-thiazolyl R^(3c) Cl Br cyano Ph CHO C(O)Me CO₂Et C(O)NMe₂Me Et i-Pr c-Pr OMe OEt OCF₃ SMe CH═CH₂ C≡CH CF₃ OPh NMe₂ NHCHO3-F-2-pyridinyl 4-Me-3-pyridinyl 2-cyano-4-pyridinyl Z-R¹ is phenyl;R^(3a) and R^(3b) are H; A is CH═C(R^(3d)); R⁴ and R⁵ are H; a is 1; R²is 2-chloro-5-thiazolyl R^(3d) CHO C(O)Me CO₂Et C(O)NMe₂ Me Et i-Pr c-PrOMe OEt OCF₃ SMe CH═CH₂ C≡CH CF₃ cyano OPh NMe₂ NHCHO Ph 3-F-2-pyridinyl4-Me-3-pyridinyl 2-cyano-4-pyridinyl Z-R¹ is phenyl; R^(3b) is H; A isO; R⁴ and R⁵ are H; a is 1; R² is 2-chloro-5-thiazolyl R^(3a) H Cl Brcyano CHO C(O)Me CO₂Et C(O)NMe₂ Me Et i-Pr c-Pr OMe OEt OCF₃ SMe CH═CH₂C≡CH CF₃ Ph OPh NMe₂ NHCHO 3-F-2-pyridinyl 4-Me-3-pyridinyl2-cyano-4-pyridinyl Z-R¹ is phenyl; R^(3b) is H; A is S; R⁴ and R⁵ areH; a is 1; R² is 2-chloro-5-thiazolyl R^(3a) H Cl Br cyano CHO C(O)MeCO₂Et C(O)NMe₂ Me Et i-Pr c-Pr OMe OEt OCF₃ SMe CH═CH₂ C≡CH CF₃ Ph OPhNMe₂ NHCHO 3-F-2-pyridinyl 4-Me-3-pyridinyl 2-cyano-4-pyridinyl Z-R¹ isphenyl; R^(3b) is H; A is NMe; R⁴ and R⁵ are H; a is 1; R² is2-chloro-5-thiazolyl R^(3a) H Cl Br cyano CHO C(O)Me CO₂Et C(O)NMe₂ MeEt i-Pr c-Pr OMe OEt OCF₃ SMe CH═CH₂ C≡CH CF₃ Ph OPh NMe₂ NHCHO3-F-2-pyridinyl 4-Me-3-pyridinyl 2-cyano-4-pyridinyl Z-R¹ is phenyl;R^(3a) and R^(3b) are H; A is NR^(3e); R⁴ and R⁵ are H; a is 1; R² is2-chloro-5-thiazolyl R^(3e) cyano NMe₂ CHO C(O)Me CO₂Et C(O)NMe₂ i-Prc-Pr OCF₃ OMe OEt CF₃ CH═CH₂ C≡CH OPh Ph 3-F-2-pyridinyl4-Me-3-pyridinyl 2-cyano-4-pyridinyl Z-R¹ is 2-fluorophenyl; R^(3b) isH; A is CH═CMe; R⁴ and R⁵ are H; a is 1; R² is 2-chloro-5-thiazolylR^(3a) H Cl Br cyano CHO C(O)Me CO₂Et C(O)NMe₂ Me Et i-Pr c-Pr OMe OEtOCF₃ SMe CH═CH₂ C≡CH CF₃ Ph OPh NMe₂ NHCHO 3-F-2-pyridinyl4-Me-3-pyridinyl 2-cyano-4-pyridinyl Z-R¹ is 2-fluorophenyl; R^(3a) isH; A is CH═CMe; R⁴ and R⁵ are H; a is 1; R² is 2-chloro-5-thiazolyl Z-R¹is 2-fluorophenyl; R^(3a) and R^(3b) are H; A is C(R^(3c))═CH; R⁴ and R⁵are H; a is 1; R² is 2-chloro-5-thiazolyl R^(3c) Cl Br cyano Ph CHOC(O)Me CO₂Et C(O)NMe₂ Me Et i-Pr c-Pr OMe OEt OCF₃ SMe CH═CH₂ C≡CH CF₃OPh NMe₂ NHCHO 3-F-2-pyridinyl 4-Me-3-pyridinyl 2-cyano-4-pyridinyl Z-R¹is 2-fluorophenyl; R^(3a) and R^(3b) are H; A is CH═C(R^(3d)); R⁴ and R⁵are H; a is 1; R² is 2-chloro-5-thiazolyl R^(3d) CHO C(O)Me CO₂EtC(O)NMe₂ Me Et i-Pr c-Pr OMe OEt OCF₃ SMe CH═CH₂ C≡CH CF₃ cyano OPh NMe₂NHCHO Ph 3-F-2-pyridinyl 4-Me-3-pyridinyl 2-cyano-4-pyridinyl Z-R¹ is2-fluorophenyl; R^(3b) is H; A is O; R⁴ and R⁵ are H; a is 1; R² is2-chloro-5-thiazolyl R^(3a) H Cl Br cyano CHO C(O)Me CO₂Et C(O)NMe₂ MeEt i-Pr c-Pr OMe OEt OCF₃ SMe CH═CH₂ C≡CH CF₃ Ph OPh NMe₂ NHCHO3-F-2-pyridinyl 4-Me-3-pyridinyl 2-cyano-4-pyridinyl Z-R¹ is2-fluorophenyl; R^(3b) is H; A is S; R⁴ and R⁵ are H; a is 1; R² is2-chloro-5-thiazolyl R^(3a) H Cl Br cyano CHO C(O)Me CO₂Et C(O)NMe₂ MeEt i-Pr c-Pr OMe OEt OCF₃ SMe CH═CH₂ C≡CH CF₃ Ph OPh NMe₂ NHCHO3-F-2-pyridinyl 4-Me-3-pyridinyl 2-cyano-4-pyridinyl Z-R¹ is2-fluorophenyl; R^(3b) is H; A is NMe; R⁴ and R⁵ are H; a is 1; R² is2-chloro-5-thiazolyl R^(3a) H Cl Br cyano CHO C(O)Me CO₂Et C(O)NMe₂ MeEt i-Pr c-Pr OMe OEt OCF₃ SMe CH═CH₂ C≡CH CF₃ Ph OPh NMe₂ NHCHO3-F-2-pyridinyl 4-Me-3-pyridinyl 2-cyano-4-pyridinyl Z-R¹ is2-fluorophenyl; R^(3a) and R^(3b) are H; A is NR^(3e); R⁴ and R⁵ are H;a is 1; R² is 2-chloro-5-thiazolyl R^(3e) cyano NMe₂ CHO C(O)Me CO₂EtC(O)NMe₂ i-Pr c-Pr OCF₃ OMe OEt CF₃ CH═CH₂ C≡CH OPh Ph 3-F-2-pyridinyl4-Me-3-pyridinyl 2-cyano-4-pyridinyl Z-R¹ is 3,5-dichlorophenyl; R^(3b)is H; A is CH═CMe; R⁴ and R⁵ are H; a is 1; R² is 2-chloro-5-thiazolylR^(3a) H Cl Br cyano CHO C(O)Me CO₂Et C(O)NMe₂ Me Et i-Pr c-Pr OMe OEtOCF₃ SMe CH═CH₂ C≡CH CF₃ Ph OPh NMe₂ NHCHO 3-F-2-pyridinyl4-Me-3-pyridinyl 2-cyano-4-pyridinyl Z-R¹ is 3,5-dichlorophenyl; R^(3a)is H; A is CH═CMe; R⁴ and R⁵ are H; a is 1; R² is 2-chloro-5-thiazolylR^(3b) Cl Br cyano Ph CHO C(O)Me CO₂Et C(O)NMe₂ Me Et i-Pr c-Pr OMe OEtOCF₃ SMe CH═CH₂ C≡CH CF₃ OPh NMe₂ NHCHO 3-F-2-pyridinyl 4-Me-3-pyridinyl2-cyano-4-pyridinyl Z-R¹ is 3,5-dichlorophenyl; R^(3a) and R^(3b) are H;A is C(R^(3c))═CH; R⁴ and R⁵ are H; a is 1; R² is 2-chloro-5-thiazolylR^(3c) Cl Br cyano Ph CHO C(O)Me CO₂Et C(O)NMe₂ Me Et i-Pr c-Pr OMe OEtOCF₃ SMe CH═CH₂ C≡CH CF₃ OPh NMe₂ NHCHO 3-F-2-pyridinyl 4-Me-3-pyridinyl2-cyano-4-pyridinyl Z-R¹ is 3,5-dichlorophenyl; R^(3a) and R^(3b) are H;A is CH═C(R^(3d)); R⁴ and R⁵ are H; a is 1; R² is 2-chloro-5-thiazolylR^(3d) CHO C(O)Me CO₂Et C(O)NMe₂ Me Et i-Pr c-Pr OMe OEt OCF₃ SMe CH═CH₂C≡CH CF₃ cyano OPh NMe₂ NHCHO Ph 3-F-2-pyridinyl 4-Me-3-pyridinyl2-cyano-4-pyridinyl Z-R¹ is 3,5-dichlorophenyl; R^(3b) is H; A is O; R⁴and R⁵ are H; a is 1; R² is 2-chloro-5-thiazolyl R^(3a) H Cl Br cyanoCHO C(O)Me CO₂Et C(O)NMe₂ Me Et i-Pr c-Pr OMe OEt OCF₃ SMe CH═CH₂ C≡CHCF₃ Ph OPh NMe₂ NHCHO 3-F-2-pyridinyl 4-Me-3-pyridinyl2-cyano-4-pyridinyl Z-R¹ is 3,5-dichlorophenyl; R^(3b) is H; A is S; R⁴and R⁵ are H; a is 1; R² is 2-chloro-5-thiazolyl R^(3a) H Cl Br cyanoCHO C(O)Me CO₂Et C(O)NMe₂ Me Et i-Pr c-Pr OMe OEt OCF₃ SMe CH═CH₂ C≡CHCF₃ Ph OPh NMe₂ NHCHO 3-F-2-pyridinyl 4-Me-3-pyridinyl2-cyano-4-pyridinyl Z-R¹ is 3,5-dichlorophenyl; R^(3b) is H; A is NMe;R⁴ and R⁵ are H; a is 1; R² is 2-chloro-5-thiazolyl R^(3a) H Cl Br cyanoCHO C(O)Me CO₂Et C(O)NMe₂ Me Et i-Pr c-Pr OMe OEt OCF₃ SMe CH═CH₂ C≡CHCF₃ Ph OPh NMe₂ NHCHO 3-F-2-pyridinyl 4-Me-3-pyridinyl2-cyano-4-pyridinyl Z-R¹ is 3,5-dichlorophenyl; R^(3a) and R^(3b) are H;A is NR^(3e); R⁴ and R⁵ are H; a is 1; R² is 2-chloro-5-thiazolyl R^(3e)cyano NMe₂ CHO C(O)Me CO₂Et C(O)NMe₂ i-Pr c-Pr OCF₃ OMe OEt CF₃ CH═CH₂C≡CH OPh Ph 3-F-2-pyridinyl 4-Me-3-pyridinyl 2-cyano-4-pyridinyl Z-R¹ is3-(trifluoromethyl)phenyl; R^(3b) is H; A is CH═CMe; R⁴ and R⁵ are H; ais 1; R² is 2-chloro-5-thiazolyl R^(3a) H Cl Br cyano CHO C(O)Me CO₂EtC(O)NMe₂ Me Et i-Pr c-Pr OMe OEt OCF₃ SMe CH═CH₂ C≡CH CF₃ Ph OPh NMe₂NHCHO 3-F-2-pyridinyl 4-Me-3-pyridinyl 2-cyano-4-pyridinyl Z-R¹ is3-(trifluoromethyl)phenyl; R^(3a) is H; A is CH═CMe; R⁴ and R⁵ are H; ais 1; R² is 2-chloro-5-thiazolyl R^(3b) Cl Br cyano Ph CHO C(O)Me CO₂EtC(O)NMe₂ Me Et i-Pr c-Pr OMe OEt OCF₃ SMe CH═CH₂ C≡CH CF₃ OPh NMe₂ NHCHO3-F-2-pyridinyl 4-Me-3-pyridinyl 2-cyano-4-pyridinyl Z-R¹ is3-(trifluoromethyl)phenyl; R^(3a) and R^(3b) are H; A is C(R^(3e))═CH;R⁴ and R⁵ are H; a is 1; R² is 2-chloro-5-thiazolyl R^(3c) Cl Br cyanoPh CHO C(O)Me CO₂Et C(O)NMe₂ Me Et i-Pr c-Pr OMe OEt OCF₃ SMe CH═CH₂C≡CH CF₃ OPh NMe₂ NHCHO 3-F-2-pyridinyl 4-Me-3-pyridinyl2-cyano-4-pyridinyl Z-R¹ is 3-(trifluoromethyl)phenyl; R^(3a) and R^(3b)are H; A is CH═C(R^(3d)); R⁴ and R⁵ are H; a is 1; R² is2-chloro-5-thiazolyl R^(3d) CHO C(O)Me CO₂Et C(O)NMe₂ Me Et i-Pr c-PrOMe OEt OCF₃ SMe CH═CH₂ C≡CH CF₃ cyano OPh NMe₂ NHCHO Ph 3-F-2-pyridinyl4-Me-3-pyridinyl 2-cyano-4-pyridinyl Z-R¹ is 3-(trifluoromethyl)phenyl;R^(3b) is H; A is O; R⁴ and R⁵ are H; a is 1; R² is 2-chloro-5-thiazolylR^(3a) H Cl Br cyano CHO C(O)Me CO₂Et C(O)NMe₂ Me Et i-Pr c-Pr OMe OEtOCF₃ SMe CH═CH₂ C≡CH CF₃ Ph OPh NMe₂ NHCHO 3-F-2-pyridinyl4-Me-3-pyridinyl 2-cyano-4-pyridinyl Z-R¹ is 3-(trifluoromethyl)phenyl;R^(3b) is H; A is S; R⁴ and R⁵ are H; a is 1; R² is 2-chloro-5-thiazolylR^(3a) H Cl Br cyano CHO C(O)Me CO₂Et C(O)NMe₂ Me Et i-Pr c-Pr OMe OEtOCF₃ SMe CH═CH₂ C≡CH CF₃ Ph OPh NMe₂ NHCHO 3-F-2-pyridinyl4-Me-3-pyridinyl 2-cyano-4-pyridinyl Z-R¹ is 3-(trifluoromethyl)phenyl;R^(3b) is H; A is NMe; R⁴ and R⁵ are H; a is 1; R² is2-chloro-5-thiazolyl R^(3a) H Cl Br cyano CHO C(O)Me CO₂Et C(O)NMe₂ MeEt i-Pr c-Pr OMe OEt OCF₃ SMe CH═CH₂ C≡CH CF₃ Ph OPh NMe₂ NHCHO3-F-2-pyridinyl 4-Me-3-pyridinyl 2-cyano-4-pyridinyl Z-R¹ is3-(trifluoromethyl)phenyl; R^(3a) and R^(3b) are H; A is NR^(3e); R⁴ andR⁵ are H; a is 1; R² is 2-chloro-5-thiazolyl R^(3e) cyano NMe₂ CHOC(O)Me CO₂Et C(O)NMe₂ i-Pr c-Pr OCF₃ OMe OEt CF₃ CH═CH₂ C≡CH OPh Ph3-F-2-pyridinyl 4-Me-3-pyridinyl 2-cyano-4-pyridinyl Z-R¹ is3-(2-chloro-4-(trifluoromethyl)phenyl)phenyl; R^(3b) is H; A is CH═CMe;R⁴ and R⁵ are H; a is 1; R² is 2-chloro-5-thiazolyl R^(3a) H Cl Br cyanoCHO C(O)Me CO₂Et C(O)NMe₂ Me Et i-Pr c-Pr OMe OEt OCF₃ SMe CH═CH₂ C≡CHCF₃ Ph OPh NMe₂ NHCHO 3-F-2-pyridinyl 4-Me-3-pyridinyl2-cyano-4-pyridinyl Z-R¹ is3-(2-chloro-4-(trifluoromethyl)phenyl)phenyl; R^(3a) is H; A is CH═CMe;R⁴ and R⁵ are H; a is 1; R² is 2-chloro-5-thiazolyl R^(3b) Cl Br cyanoPh CHO C(O)Me CO₂Et C(O)NMe₂ Me Et i-Pr c-Pr OMe OEt OCF₃ SMe CH═CH₂C≡CH CF₃ OPh NMe₂ NHCHO 3-F-2-pyridinyl 4-Me-3-pyridinyl2-cyano-4-pyridinyl Z-R¹ is3-(2-chloro-4-(trifluoromethyl)phenyl)phenyl; R^(3a) and R^(3b) are H; Ais C(R^(3c))═CH; R⁴ and R⁵ are H; a is 1; R² is 2-chloro-5-thiazolylR^(3c) Cl Br cyano Ph CHO C(O)Me CO₂Et C(O)NMe₂ Me Et i-Pr c-Pr OMe OEtOCF₃ SMe CH═CH₂ C≡CH CF₃ OPh NMe₂ NHCHO 3-F-2-pyridinyl 4-Me-3-pyridinyl2-cyano-4-pyridinyl Z-R¹ is3-(2-chloro-4-(trifluoromethyl)phenyl)phenyl; R^(3a) and R^(3b) are H; Ais CH═C(R^(3d)); R⁴ and R⁵ are H; a is 1; R² is 2-chloro-5-thiazolylR^(3d) CHO C(O)Me CO₂Et C(O)NMe₂ Me Et i-Pr c-Pr OMe OEt OCF₃ SMe CH═CH₂C≡CH CF₃ cyano OPh NMe₂ NHCHO Ph 3-F-2-pyridinyl 4-Me-3-pyridinyl2-cyano-4-pyridinyl Z-R¹ is3-(2-chloro-4-(trifluoromethyl)phenyl)phenyl; R^(3b) is H; A is O; R⁴and R⁵ are H; a is 1; R² is 2-chloro-5-thiazolyl R^(3a) H Cl Br cyanoCHO C(O)Me CO₂Et C(O)NMe₂ Me Et i-Pr c-Pr OMe OEt OCF₃ SMe CH═CH₂ C≡CHCF₃ Ph OPh NMe₂ NHCHO 3-F-2-pyridinyl 4-Me-3-pyridinyl2-cyano-4-pyridinyl Z-R¹ is3-(2-chloro-4-(trifluoromethyl)phenyl)phenyl; R^(3b) is H; A is S; R⁴and R⁵ are H; a is 1; R² is 2-chloro-5-thiazolyl R^(3a) H Cl Br cyanoCHO C(O)Me CO₂Et C(O)NMe₂ Me Et i-Pr c-Pr OMe OEt OCF₃ SMe CH═CH₂ C≡CHCF₃ Ph OPh NMe₂ NHCHO 3-F-2-pyridinyl 4-Me-3-pyridinyl2-cyano-4-pyridinyl Z-R¹ is3-(2-chloro-4-(trifluoromethyl)phenyl)phenyl; R^(3b) is H; A is NMe; R⁴and R⁵ are H; a is 1; R² is 2-chloro-5-thiazolyl R^(3a) H Cl Br cyanoCHO C(O)Me CO₂Et C(O)NMe₂ Me Et i-Pr c-Pr OMe OEt OCF₃ SMe CH═CH₂ C≡CHCF₃ Ph OPh NMe₂ NHCHO 3-F-2-pyridinyl 4-Me-3-pyridinyl2-cyano-4-pyridinyl Z-R¹ is3-(2-chloro-4-(trifluoromethyl)phenyl)phenyl; R^(3a) and R^(3b) are H; Ais NR^(3e); R⁴ and R⁵ are H; a is 1; R² is 2-chloro-5-thiazolyl R^(3e)cyano NMe₂ CHO C(O)Me CO₂Et C(O)NMe₂ i-Pr c-Pr OCF₃ OMe OEt CF₃ CH═CH₂C≡CH OPh Ph 3-F-2-pyridinyl 4-Me-3-pyridinyl 2-cyano-4-pyridinyl

TABLE 20

ZR¹ A is NCH₂CHF₂; R² is 2-chloro-5-thiazolyl Ph 2-F—Ph 3-CN—Ph 3-MeO—PhC(O)CF₃ C(O)Ph 3-CF₃—Ph 3-CO₂Et—Ph CO₂Et 3-CF₃O—Ph 3-C(O)NMe₂—Ph3,5-diCl—Ph 3-Cl, 5-CF₃—Ph 3-Me—Ph 3-(2-Cl-4-CF₃—Ph)Ph A is NCH₂CHF₂; R²is 2-methyl-5-thiazolyl Ph 2-F—Ph 3-CN—Ph 3-MeO—Ph C(O)CF₃ C(O)Ph3-CF₃—Ph 3-CO₂Et—Ph CO₂Et 3-CF₃O—Ph 3-C(O)NMe₂—Ph 3,5-diCl—Ph 3-Cl,5-CF₃—Ph 3-Me—Ph 3-(2-Cl-4-CF₃—Ph)Ph A is NCH₂CHF₂; R² is 5-thiazolyl Ph2-F—Ph 3-CN—Ph 3-MeO—Ph C(O)CF₃ C(O)Ph 3-CF₃—Ph 3-CO₂Et—Ph CO₂Et3-CF₃O—Ph 3-C(O)NMe₂—Ph 3,5-diCl—Ph 3-Cl, 5-CF₃—Ph 3-Me—Ph3-(2-Cl-4-CF₃—Ph)Ph A is NCH₂CHF₂; R² is CF₃ Ph 2-F—Ph 3-CN—Ph 3-MeO—PhC(O)CF₃ C(O)Ph 3-CF₃—Ph 3-CO₂Et—Ph CO₂Et 3-CF₃O—Ph 3-C(O)NMe₂—Ph3,5-diCl—Ph 3-Cl, 5-CF₃—Ph 3-Me—Ph 3-(2-Cl-4-CF₃—Ph)Ph A is NCH₂CHF₂; R²is 6-chloro-3-pyridinyl Ph 2-F—Ph 3-CN—Ph 3-MeO—Ph C(O)CF₃ C(O)Ph3-CF₃—Ph 3-CO₂Et—Ph CO₂Et 3-CF₃O—Ph 3-C(O)NMe₂—Ph 3,5-diCl—Ph 3-Cl,5-CF₃—Ph 3-Me—Ph 3-(2-Cl-4-CF₃—Ph)Ph A is NCH₂CHF₂; R² is6-fluoro-3-pyridinyl Ph 2-F—Ph 3-CN—Ph 3-MeO—Ph C(O)CF₃ C(O)Ph 3-CF₃—Ph3-CO₂Et—Ph CO₂Et 3-CF₃O—Ph 3-C(O)NMe₂—Ph 3,5-diCl—Ph 3-Cl, 5-CF₃—Ph3-Me—Ph 3-(2-Cl-4-CF₃—Ph)Ph A is NCH₂CHF₂; R² is 1-methyl-4-pyrazoyl Ph2-F—Ph 3-CN—Ph 3-MeO—Ph C(O)CF₃ C(O)Ph 3-CF₃—Ph 3-CO₂Et—Ph CO₂Et3-CF₃O—Ph 3-C(O)NMe₂—Ph 3,5-diCl—Ph 3-Cl, 5-CF₃—Ph 3-Me—Ph3-(2-Cl-4-CF₃—Ph)Ph A is NEt; R² is 2-chloro-5-thiazolyl Ph 2-F—Ph3-CN—Ph 3-MeO—Ph C(O)CF₃ C(O)Ph 3-CF₃—Ph 3-CO₂Et—Ph CO₂Et 3-CF₃O—Ph3-C(O)NMe₂—Ph 3,5-diCl—Ph 3-Cl, 5-CF₃—Ph 3-Me—Ph 3-(2-Cl-4-CF₃—Ph)Ph Ais NEt; R² is 2-methyl-5-thiazolyl Ph 2-F—Ph 3-CN—Ph 3-MeO—Ph C(O)CF₃C(O)Ph 3-CF₃—Ph 3-CO₂Et—Ph CO₂Et 3-CF₃O—Ph 3-C(O)NMe₂—Ph 3,5-diCl—Ph3-Cl, 5-CF₃—Ph 3-Me—Ph 3-(2-Cl-4-CF₃—Ph)Ph A is NEt; R²is 5-thiazolyl Ph2-F—Ph 3-CN—Ph 3-MeO—Ph C(O)CF₃ C(O)Ph 3-CF₃—Ph 3-CO₂Et—Ph CO₂Et3-CF₃O—Ph 3-C(O)NMe₂—Ph 3,5-diCl—Ph 3-Cl, 5-CF₃—Ph 3-Me—Ph3-(2-Cl-4-CF₃—Ph)Ph A is NEt; R² is CF₃ Ph 2-F—Ph 3-CN—Ph 3-MeO—PhC(O)CF₃ C(O)Ph 3-CF₃—Ph 3-CO₂Et—Ph CO₂Et 3-CF₃O—Ph 3-C(O)NMe₂—Ph3,5-diCl—Ph 3-Cl, 5-CF₃—Ph 3-Me—Ph 3-(2-Cl-4-CF₃—Ph)Ph A is NEt; R² is6-chloro-3-pyridinyl Ph 2-F—Ph 3-CN—Ph 3-MeO—Ph C(O)CF₃ C(O)Ph 3-CF₃—Ph3-CO₂Et—Ph CO₂Et 3-CF₃O—Ph 3-C(O)NMe₂—Ph 3,5-diCl—Ph 3-Cl, 5-CF₃—Ph3-Me—Ph 3-(2-Cl-4-CF₃—Ph)Ph A is NEt; R² is 6-fluoro-3-pyridinyl Ph2-F—Ph 3-CN—Ph 3-MeO—Ph C(O)CF₃ C(O)Ph 3-CF₃—Ph 3-CO₂Et—Ph CO₂Et3-CF₃O—Ph 3-C(O)NMe₂—Ph 3,5-diCl—Ph 3-Cl, 5-CF₃—Ph 3-Me—Ph3-(2-Cl-4-CF₃—Ph)Ph A is NEt; R² is 1-methyl-4-pyrazolyl Ph 2-F—Ph3-CN—Ph 3-MeO—Ph C(O)CF₃ C(O)Ph 3-CF₃—Ph 3-CO₂Et—Ph CO₂Et 3-CF₃O—Ph3-C(O)NMe₂—Ph 3,5-diCl—Ph 3-Cl, 5-CF₃—Ph 3-Me—Ph 3-(2-Cl-4-CF₃—Ph)Ph Ais NCH₂CF₃; R² is H Ph 2-F—Ph 3-CN—Ph 3-MeO—Ph C(O)CF₃ C(O)Ph 3-CF₃—Ph3-CO₂Et—Ph CO₂Et 3-CF₃O—Ph 3-C(O)NMe₂—Ph 3,5-diCl—Ph 3-Cl, 5-CF₃—Ph3-Me—Ph 3-(2-Cl-4-CF₃—Ph)Ph A is NCH₂(6-chloro-3-pyridinyl); R² is H Ph2-F—Ph 3-CN—Ph 3-MeO—Ph C(O)CF₃ C(O)Ph 3-CF₃—Ph 3-CO₂Et—Ph CO₂Et3-CF₃O—Ph 3-C(O)NMe₂—Ph 3,5-diCl—Ph 3-Cl, 5-CF₃—Ph 3-Me—Ph3-(2-Cl-4-CF₃—Ph)Ph A is NCH₂(6-fluoro-3-pyridinyl); R² is H Ph 2-F—Ph3-CN—Ph 3-MeO—Ph C(O)CF₃ C(O)Ph 3-CF₃—Ph 3-CO₂Et—Ph CO₂Et 3-CF₃O—Ph3-C(O)NMe₂—Ph 3,5-diCl—Ph 3-Cl, 5-CF₃—Ph 3-Me—Ph 3-(2-Cl-4-CF₃—Ph)Ph Ais NCH₂(2-chloro-5-thiazolyl); R² is H Ph 2-F—Ph 3-CN—Ph 3-MeO—PhC(O)CF₃ C(O)Ph 3-CF₃—Ph 3-CO₂Et—Ph CO₂Et 3-CF₃O—Ph 3-C(O)NMe₂—Ph3,5-diCl—Ph 3-Cl, 5-CF₃—Ph 3-Me—Ph 3-(2-Cl-4-CF₃—Ph)Ph A is NCH₂CF₃; R²is Me Ph 2-F—Ph 3-CN—Ph 3-MeO—Ph C(O)CF₃ C(O)Ph 3-CF₃—Ph 3-CO₂Et—PhCO₂Et 3-CF₃O—Ph 3-C(O)NMe₂—Ph 3,5-diCl—Ph 3-Cl, 5-CF₃—Ph 3-Me—Ph3-(2-Cl-4-CF₃—Ph)Ph A is NCH₂(6-chloro-3-pyridinyl); R² is Me Ph 2-F—Ph3-CN—Ph 3-MeO—Ph C(O)CF₃ C(O)Ph 3-CF₃—Ph 3-CO₂Et—Ph CO₂Et 3-CF₃O—Ph3-C(O)NMe₂—Ph 3,5-diCl—Ph 3-Cl, 5-CF₃—Ph 3-Me—Ph 3-(2-Cl-4-CF₃—Ph)Ph Ais NCH₂(6-fluoro-3-pyridinyl); R² is Me Ph 2-F—Ph 3-CN—Ph 3-MeO—PhC(O)CF₃ C(O)Ph 3-CF₃—Ph 3-CO₂Et—Ph CO₂Et 3-CF₃O—Ph 3-C(O)NMe₂—Ph3,5-diCl—Ph 3-Cl, 5-CF₃—Ph 3-Me—Ph 3-(2-Cl-4-CF₃—Ph)Ph A isNCH₂(2-chloro-5-thiazolyl); R² is Me Ph 2-F—Ph 3-CN—Ph 3-MeO—Ph C(O)CF₃C(O)Ph 3-CF₃—Ph 3-CO₂Et—Ph CO₂Et 3-CF₃O—Ph 3-C(O)NMe₂—Ph 3,5-diCl—Ph3-Cl, 5-CF₃—Ph 3-Me—Ph 3-(2-Cl-4-CF₃—Ph)Ph

TABLE 21

ZR¹ R⁴ is F; R² is 2-chloro-5-thiazolyl Ph 2-F—Ph 3-CN—Ph 3-MeO—PhC(O)CF₃ C(O)Ph 3-CF₃—Ph 3-CO₂Et—Ph CO₂Et 3-CF₃O—Ph 3-C(O)NMe₂—Ph3,5-diCl—Ph 3-Cl, 5-CF₃—Ph 3-Me—Ph 3-(2-Cl-4-CF₃—Ph)Ph R⁴ is F; R² is2-methyl-5-thiazolyl Ph 2-F—Ph 3-CN—Ph 3-MeO—Ph C(O)CF₃ C(O)Ph 3-CF₃—Ph3-CO₂Et—Ph CO₂Et 3-CF₃O—Ph 3-C(O)NMe₂—Ph 3,5-diCl—Ph 3-Cl, 5-CF₃—Ph3-Me—Ph 3-(2-Cl-4-CF₃—Ph)Ph R⁴ is F; R² is CF₃ Ph 2-F—Ph 3-CN—Ph3-MeO—Ph C(O)CF₃ C(O)Ph 3-CF₃—Ph 3-CO₂Et—Ph CO₂Et 3-CF₃O—Ph3-C(O)NMe₂—Ph 3,5-diCl—Ph 3-Cl, 5-CF₃—Ph 3-Me—Ph 3-(2-Cl-4-CF₃—Ph)Ph R⁴is F; R² is 6-chloro-3-pyridinyl Ph 2-F—Ph 3-CN—Ph 3-MeO—Ph C(O)CF₃C(O)Ph 3-CF₃—Ph 3-CO₂Et—Ph CO₂Et 3-CF₃O—Ph 3-C(O)NMe₂—Ph 3,5-diCl—Ph3-Cl, 5-CF₃—Ph 3-Me—Ph 3-(2-Cl-4-CF₃—Ph)Ph R4 is F; R2 is6-fluoro-3-pyridinyl Ph 2-F—Ph 3-CN—Ph 3-MeO—Ph C(O)CF₃ C(O)Ph 3-CF₃—Ph3-CO₂Et—Ph CO₂Et 3-CF₃O—Ph 3-C(O)NMe₂—Ph 3,5-diCl—Ph 3-Cl, 5-CF₃—Ph3-Me—Ph 3-(2-Cl-4-CF₃—Ph)Ph R⁴ is F; R² is 1-methyl-4-pyrazolyl Ph2-F—Ph 3-CN—Ph 3-MeO—Ph C(O)CF₃ C(O)Ph 3-CF₃—Ph 3-CO₂Et—Ph CO₂Et3-CF₃O—Ph 3-C(O)NMe₂—Ph 3,5-diCl—Ph 3-Cl, 5-CF₃—Ph 3-Me—Ph3-(2-Cl-4-CF₃—Ph)Ph

TABLE 22

R⁴ R⁵ is H Cl Br cyano Ph CHO C(O)Me CO₂Et C(O)NMe₂ Et i-Pr c-Pr CF₃ OMeOEt OCF₃ CH═CH₂ C≡CH SMe OPh NMe₂ NHCHO 3-F-2-pyridinyl 4-Me-3-pyridinyl2-cyano-4-pyridinyl R⁵ is Me Cl Br cyano Ph CHO C(O)Me CO₂Et C(O)NMe₂ Eti-Pr c-Pr CF₃ OMe OEt OCF₃ CH═CH₂ C≡CH SMe OPh NMe₂ NHCHO3-F-2-pyridinyl 4-Me-3-pyridinyl 2-cyano-4-pyridinyl R⁵ is c-Pr Cl Brcyano Ph CHO C(O)Me CO₂Et C(O)NMe₂ Et i-Pr c-Pr CF₃ OMe OEt OCF₃ CH═CH₂C≡CH SMe OPh NMe₂ NHCHO 3-F-2-pyridinyl 4-Me-3-pyridinyl2-cyano-4-pyridinyl

TABLE 23

ZR¹ a is 2; R² is 2-chloro-5-thiazolyl Ph 2-F—Ph 3-CN—Ph 3-MeO—PhC(O)CF₃ C(O)Ph 3-CF₃—Ph 3-CO₂Et—Ph CO₂Et 3-CF₃O—Ph 3-C(O)NMe₂—Ph3,5-diCl—Ph 3-Cl, 5-CF₃—Ph 3-Me—Ph 3-(2-Cl-4-CF₃—Ph)Ph a is 2; R² is2-methyl-5-thiazolyl Ph 2-F—Ph 3-CN—Ph 3-MeO—Ph C(O)CF₃ C(O)Ph 3-CF₃—Ph3-CO₂Et—Ph CO₂Et 3-CF₃O—Ph 3-C(O)NMe₂—Ph 3,5-diCl—Ph 3-Cl, 5-CF₃—Ph3-Me—Ph 3-(2-Cl-4-CF₃—Ph)Ph a is 2; R² is 5-thiazolyl Ph 2-F—Ph 3-CN—Ph3-MeO—Ph C(O)CF₃ C(O)Ph 3-CF₃—Ph 3-CO₂Et—Ph CO₂Et 3-CF₃O—Ph3-C(O)NMe₂—Ph 3,5-diCl—Ph 3-Cl, 5-CF₃—Ph 3-Me—Ph 3-(2-Cl-4-CF₃—Ph)Ph ais 2; R² is 2-fluoro-5-thiazolyl Ph 2-F—Ph 3-CN—Ph 3-MeO—Ph C(O)CF₃C(O)Ph 3-CF₃—Ph 3-CO₂Et—Ph CO₂Et 3-CF₃O—Ph 3-C(O)NMe₂—Ph 3,5-diCl—Ph3-Cl, 5-CF₃—Ph 3-Me—Ph 3-(2-Cl-4-CF₃—Ph)Ph a is 2; R² is 5-pyrimidinylPh 2-F—Ph 3-CN—Ph 3-MeO—Ph C(O)CF₃ C(O)Ph 3-CF₃—Ph 3-CO₂Et—Ph CO₂Et3-CF₃O—Ph 3-C(O)NMe₂—Ph 3,5-diCl—Ph 3-Cl, 5-CF₃—Ph 3-Me—Ph3-(2-Cl-4-CF₃—Ph)Ph a is 2; R² is 2-methyl-5-pyrimidinyl Ph 2-F—Ph3-CN—Ph 3-MeO—Ph C(O)CF₃ C(O)Ph 3-CF₃—Ph 3-CO₂Et—Ph CO₂Et 3-CF₃O—Ph3-C(O)NMe₂—Ph 3,5-diCl—Ph 3-Cl, 5-CF₃—Ph 3-Me—Ph 3-(2-Cl-4-CF₃—Ph)Ph ais 2; R² is CF₃ Ph 2-F—Ph 3-CN—Ph 3-MeO—Ph C(O)CF₃ C(O)Ph 3-CF₃—Ph3-CO₂Et—Ph CO₂Et 3-CF₃O—Ph 3-C(O)NMe₂—Ph 3,5-diCl—Ph 3-Cl, 5-CF₃—Ph3-Me—Ph 3-(2-Cl-4-CF₃—Ph)Ph a is 2; R² is 6-chloro-3-pyridinyl Ph 2-F—Ph3-CN—Ph 3-MeO—Ph C(O)CF₃ C(O)Ph 3-CF₃—Ph 3-CO₂Et—Ph CO₂Et 3-CF₃O—Ph3-C(O)NMe₂—Ph 3,5-diCl—Ph 3-Cl, 5-CF₃—Ph 3-Me—Ph 3-(2-Cl-4-CF₃—Ph)Ph ais 2; R² is 6-fluoro-3-pyridinyl Ph 2-F—Ph 3-CN—Ph 3-MeO—Ph C(O)CF₃C(O)Ph 3-CF₃—Ph 3-CO₂Et—Ph CO₂Et 3-CF₃O—Ph 3-C(O)NMe₂—Ph 3,5-diCl—Ph3-Cl, 5-CF₃—Ph 3-Me—Ph 3-(2-Cl-4-CF₃—Ph)Ph a is 2; R² is-methyl-4-pyrazolyl Ph 2-F—Ph 3-CN—Ph 3-MeO—Ph C(O)CF₃ C(O)Ph 3-CF₃—Ph3-CO₂Et—Ph CO₂Et 3-CF₃O—Ph 3-C(O)NMe₂—Ph 3,5-diCl—Ph 3-Cl, 5-CF₃—Ph3-Me—Ph 3-(2-Cl-4-CF₃—Ph)Ph a is 3; R² is 2-chloro-5-thiazolyl Ph 2-F—Ph3-CN—Ph 3-MeO—Ph C(O)CF₃ C(O)Ph 3-CF₃—Ph 3-CO₂Et—Ph CO₂Et 3-CF₃O—Ph3-C(O)NMe₂—Ph 3,5-diCl—Ph 3-Cl, 5-CF₃—Ph 3-Me—Ph 3-(2-Cl-4-CF₃—Ph)Ph ais 3; R² is 2-methyl-5-thiazolyl Ph 2-F—Ph 3-CN—Ph 3-MeO—Ph C(O)CF₃C(O)Ph 3-CF₃—Ph 3-CO₂Et—Ph CO₂Et 3-CF₃O—Ph 3-C(O)NMe₂—Ph 3,5-diCl—Ph3-Cl, 5-CF₃—Ph 3-Me—Ph 3-(2-Cl-4-CF₃—Ph)Ph a is 3; R² is 5-thiazolyl Ph2-F—Ph 3-CN—Ph 3-MeO—Ph C(O)CF₃ C(O)Ph 3-CF₃—Ph 3-CO₂Et—Ph CO₂Et3-CF₃O—Ph 3-C(O)NMe₂—Ph 3,5-diCl—Ph 3-Cl, 5-CF₃—Ph 3-Me—Ph3-(2-Cl-4-CF₃—Ph)Ph a is 3; R² is CF₃ Ph 2-F—Ph 3-CN—Ph 3-MeO—Ph C(O)CF₃C(O)Ph 3-CF₃—Ph 3-CO₂Et—Ph CO₂Et 3-CF₃O—Ph 3-C(O)NMe₂—Ph 3,5-diCl—Ph3-Cl, 5-CF₃—Ph 3-Me—Ph 3-(2-Cl-4-CF₃—Ph)Ph a is 3; R² is6-fluoro-3-pyridinyl Ph 2-F—Ph 3-CN—Ph 3-MeO—Ph C(O)CF₃ C(O)Ph 3-CF₃—Ph3-CO₂Et—Ph CO₂Et 3-CF₃O—Ph 3-C(O)NMe₂—Ph 3,5-diCl—Ph 3-Cl, 5-CF₃—Ph3-Me—Ph 3-(2-Cl-4-CF₃—Ph)Ph a is 3; R² is 1-methyl-4-pyrazolyl Ph 2-F—Ph3-CN—Ph 3-MeO—Ph C(O)CF₃ C(O)Ph 3-CF₃—Ph 3-CO₂Et—Ph CO₂Et 3-CF₃O—Ph3-C(O)NMe₂—Ph 3,5-diCl—Ph 3-Cl, 5-CF₃—Ph 3-Me—Ph 3-(2-Cl-4-CF₃—Ph)Ph

TABLE 24

R² R is 2-F cyano CHO Ph C(O)Me CO₂Et C(O)NMe₂ Et i-Pr c-Pr CH₂OMeCH₂OEt CH₂OCF₃ CH═CH₂ C≡CH CH₂SMe OPh CH₂NMe₂ CH₂NHCHO 3-F-2-pyridinyl4-Me-3-pyridinyl 2-cyano-4-pyridinyl R is 3-Me cyano CHO Ph C(O)Me CO₂EtC(O)NMe₂ Et i-Pr c-Pr CH₂OMe CH₂OEt CH₂OCF₃ CH═CH₂ C≡CH CH₂SMe OPhCH₂NMe₂ CH₂NHCHO 3-F-2-pyridinyl 4-Me-3-pyridinyl 2-cyano-4-pyridinyl Ris 3-CN cyano CHO Ph C(O)Me CO₂Et C(O)NMe₂ Et i-Pr c-Pr CH₂OMe CH₂OEtCH₂OCF₃ CH═CH₂ C≡CH CH₂SMe OPh CH₂NMe₂ CH₂NHCHO 3-F-2-pyridinyl4-Me-3-pyridinyl 2-cyano-4-pyridinyl R is 3-OMe cyano CHO Ph C(O)MeCO₂Et C(O)NMe₂ Et i-Pr c-Pr CH₂OMe CH₂OEt CH₂OCF₃ CH═CH₂ C≡CH CH₂SMe OPhCH₂NMe₂ CH₂NHCHO 3-F-2-pyridinyl 4-Me-3-pyridinyl 2-cyano-4-pyridinyl Ris 3-CF₃ cyano CHO Ph C(O)Me CO₂Et C(O)NMe₂ Et i-Pr c-Pr CH₂OMe CH₂OEtCH₂OCF₃ CH═CH₂ C≡CH CH₂SMe OPh CH₂NMe₂ CH₂NHCHO 3-F-2-pyridinyl4-Me-3-pyridinyl 2-cyano-4-pyridinyl R is 3-Cl, 5-Cl cyano CHO Ph C(O)MeCO₂Et C(O)NMe₂ Et i-Pr c-Pr CH₂OMe CH₂OEt CH₂OCF₃ CH═CH₂ C≡CH CH₂SMe OPhCH₂NMe₂ CH₂NHCHO 3-F-2-pyridinyl 4-Me-3-pyridinyl 2-cyano-4-pyridinyl Ris 3-(2-chloro-4-(trifluoromethyl)phenyl) cyano CHO Ph C(O)Me CO₂EtC(O)NMe₂ Et i-Pr c-Pr CH₂OMe CH₂OEt CH₂OCF₃ CH═CH₂ C≡CH CH₂SMe OPhCH₂NMe₂ CH₂NHCHO 3-F-2-pyridinyl 4-Me-3-pyridinyl 2-cyano-4-pyridinyl

TABLE 25

R R^(a) is 2-F cyano CHO Ph CF₃ C(O)Me CO₂Et C(O)NMe₂ Et i-Pr c-Pr OMeOEt OCF₃ CH═CH₂ C≡CH SMe OPh NMe₂ NHCHO 3-F-2-pyridinyl 4-Me-3-pyridinyl2-cyano-4-pyridinyl R^(a) is 3-Me cyano CHO Ph CF₃ C(O)Me CO₂Et C(O)NMe₂Et i-Pr c-Pr OMe OEt OCF₃ CH═CH₂ C≡CH SMe OPh NMe₂ NHCHO 3-F-2-pyridinyl4-Me-3-pyridinyl 2-cyano-4-pyridinyl R^(a) is 3-CN cyano CHO Ph CF₃C(O)Me CO₂Et C(O)NMe₂ Et i-Pr c-Pr OMe OEt OCF₃ CH═CH₂ C≡CH SMe OPh NMe₂NHCHO 3-F-2-pyridinyl 4-Me-3-pyridinyl 2-cyano-4-pyridinyl R^(a) is3-OMe cyano CHO Ph CF₃ C(O)Me CO₂Et C(O)NMe₂ Et i-Pr c-Pr OMe OEt OCF₃CH═CH₂ C≡CH SMe OPh NMe₂ NHCHO 3-F-2-pyridinyl 4-Me-3-pyridinyl2-cyano-4-pyridinyl R^(a) is 3-CF₃ cyano CHO Ph CF₃ C(O)Me CO₂EtC(O)NMe₂ Et i-Pr c-Pr OMe OEt OCF₃ CH═CH₂ C≡CH SMe OPh NMe₂ NHCHO3-F-2-pyridinyl 4-Me-3-pyridinyl 2-cyano-4-pyridinyl R^(a) is 3-Cl, 5-Clcyano CHO Ph CF₃ C(O)Me CO₂Et C(O)NMe₂ Et i-Pr c-Pr OMe OEt OCF₃ CH═CH₂C≡CH SMe OPh NMe₂ NHCHO 3-F-2-pyridinyl 4-Me-3-pyridinyl2-cyano-4-pyridinyl R^(a) is 3-(2-chloro-4-(trifluoromethyl)phenyl)cyano CHO Ph CF₃ C(O)Me CO₂Et C(O)NMe₂ Et i-Pr c-Pr OMe OEt OCF₃ CH═CH₂C≡CH SMe OPh NMe₂ NHCHO 3-F-2-pyridinyl 4-Me-3-pyridinyl2-cyano-4-pyridinyl

TABLE 26

R R^(a) is 2-F cyano CHO Ph CF₃ C(O)Me CO₂Et C(O)NMe₂ Et i-Pr c-Pr OMeOEt OCF₃ CH═CH₂ C≡CH SMe OPh NMe₂ NHCHO 3-F-2-pyridinyl 4-Me-3-pyridinyl2-cyano-4-pyridinyl R^(a) is 3-Me cyano CHO Ph CF₃ C(O)Me CO₂Et C(O)NMe₂Et i-Pr c-Pr OMe OEt OCF₃ CH═CH₂ C≡CH SMe OPh NMe₂ NHCHO 3-F-2-pyridinyl4-Me-3-pyridinyl 2-cyano-4-pyridinyl R^(a) is 3-CN cyano CHO Ph CF₃C(O)Me CO₂Et C(O)NMe₂ Et i-Pr c-Pr OMe OEt OCF₃ CH═CH₂ C≡CH SMe OPh NMe₂NHCHO 3-F-2-pyridinyl 4-Me-3-pyridinyl 2-cyano-4-pyridinyl R^(a) is3-OMe cyano CHO Ph CF₃ C(O)Me CO₂Et C(O)NMe₂ Et i-Pr c-Pr OMe OEt OCF₃CH═CH₂ C≡CH SMe OPh NMe₂ NHCHO 3-F-2-pyridinyl 4-Me-3-pyridinyl2-cyano-4-pyridinyl R^(a) is 3-CF₃ cyano CHO Ph CF₃ C(O)Me CO₂EtC(O)NMe₂ Et i-Pr c-Pr OMe OEt OCF₃ CH═CH₂ C≡CH SMe OPh NMe₂ NHCHO3-F-2-pyridinyl 4-Me-3-pyridinyl 2-cyano-4-pyridinyl R^(a) is 3-Cl, 5-Clcyano CHO Ph CF₃ C(O)Me CO₂Et C(O)NMe₂ Et i-Pr c-Pr OMe OEt OCF₃ CH═CH₂C≡CH SMe OPh NMe₂ NHCHO 3-F-2-pyridinyl 4-Me-3-pyridinyl2-cyano-4-pyridinyl R^(a) is 3-(2-chloro-4-(trifluoromethyl)phenyl)cyano CHO Ph CF₃ C(O)Me CO₂Et C(O)NMe₂ Et i-Pr c-Pr OMe OEt OCF₃ CH═CH₂C≡CH SMe OPh NMe₂ NHCHO 3-F-2-pyridinyl 4-Me-3-pyridinyl2-cyano-4-pyridinyl

TABLE 27

R R^(a) is 2-F cyano CHO Ph CF₃ C(O)Me CO₂Et C(O)NMe₂ Me Et i-Pr c-Pr ClOMe OEt OCF₃ Br CH═CH₂ C≡CH SMe OPh NMe₂ NHCHO 3-F-2-pyridinyl4-Me-3-pyridinyl 2-cyano-4-pyridinyl R^(a) is 3-Me cyano CHO Ph CF₃C(O)Me CO₂Et C(O)NMe₂ Me Et i-Pr c-Pr Cl OMe OEt OCF₃ Br CH═CH₂ C≡CH SMeOPh NMe₂ NHCHO 3-F-2-pyridinyl 4-Me-3-pyridinyl 2-cyano-4-pyridinylR^(a) is 3-CN cyano CHO Ph CF₃ C(O)Me CO₂Et C(O)NMe₂ Me Et i-Pr c-Pr ClOMe OEt OCF₃ Br CH═CH₂ C≡CH SMe OPh NMe₂ NHCHO 3-F-2-pyridinyl4-Me-3-pyridinyl 2-cyano-4-pyridinyl R^(a) is 3-OMe cyano CHO Ph CF₃C(O)Me CO₂Et C(O)NMe₂ Me Et i-Pr c-Pr Cl OMe OEt OCF₃ Br CH═CH₂ C≡CH SMeOPh NMe₂ NHCHO 3-F-2-pyridinyl 4-Me-3-pyridinyl 2-cyano-4-pyridinylR^(a) is 3-CF₃ cyano CHO Ph CF₃ C(O)Me CO₂Et C(O)NMe₂ Me Et i-Pr c-Pr ClOMe OEt OCF₃ Br CH═CH₂ C≡CH SMe OPh NMe₂ NHCHO 3-F-2-pyridinyl4-Me-3-pyridinyl 2-cyano-4-pyridinyl R^(a) is 3-Cl, 5-Cl cyano CHO PhCF₃ C(O)Me CO₂Et C(O)NMe₂ Me Et i-Pr c-Pr Cl OMe OEt OCF₃ Br CH═CH₂ C≡CHSMe OPh NMe₂ NHCHO 3-F-2-pyridinyl 4-Me-3-pyridinyl 2-cyano-4-pyridinylR^(a) is 3-(2-chloro-4-(trifluoromethyl)phenyl) cyano CHO Ph CF₃ C(O)MeCO₂Et C(O)NMe₂ Me Et i-Pr c-Pr Cl OMe OEt OCF₃ Br CH═CH₂ C≡CH SMe OPhNMe₂ NHCHO 3-F-2-pyridinyl 4-Me-3-pyridinyl 2-cyano-4-pyridinyl

TABLE 28

ZR¹ R² is 2-chloro-5-thiazolyl Cl F CF₃ Me c-Pr C(O)Me Br C(O)NMe₂c-Pr-2-(c-Pr) CH═CH₂ C(O)CF₃ CHO I NMe₂ Et C≡CH C(O)Ph CO₂Et cyano NHCHOi-Pr 2-thienyl 3-thienyl 4-CF₃-2-thiazolyl 5-CF₃-2-thiazolyl2-CF₃-4-thiazolyl 5-CF₃-4-thiazolyl C(O)(2-F—Ph) C(O)(3-CF₃—Ph)2-CF₃-5-thiazolyl 4-CF₃-5-thiazolyl 1-Me-5-CF₃-2-imidazolyl1-Me-4-CF₃-2-imidazolyl C(O)(3,5-diCl—Ph) C(O)(3-(2-Cl-4-CF₃—Ph)Ph) R²is 6-chloro-3-pyridinyl Cl F CF₃ Me c-Pr C(O)Me Br C(O)NMe₂c-Pr-2-(c-Pr) CH═CH₂ C(O)CF₃ CHO I NMe₂ Et C≡CH C(O)Ph CO₂Et cyano NHCHOi-Pr 2-thienyl 3-thienyl 4-CF₃-2-thiazolyl 5-CF₃-2-thiazolyl2-CF₃-4-thiazolyl 5-CF₃-4-thiazolyl C(O)(2-F—Ph) C(O)(3-CF₃—Ph)2-CF₃-5-thiazolyl 4-CF₃-5-thiazolyl 1-Me-5-CF₃-2-imidazolyl1-Me-4-CF₃-2-imidazolyl C(O)(3,5-diCl—Ph) C(O)(3-(2-Cl-4-CF₃—Ph)Ph) R²is 6-fluoro-3-pyridinyl Cl F CF₃ Me c-Pr C(O)Me Br C(O)NMe₂c-Pr-2-(c-Pr) CH═CH₂ C(O)CF₃ CHO I NMe₂ Et C≡CH C(O)Ph CO₂Et cyano NHCHOi-Pr 2-thienyl 3-thienyl 4-CF₃-2-thiazolyl 5-CF₃-2-thiazolyl2-CF₃-4-thiazolyl 5-CF₃-4-thiazolyl C(O)(2-F—Ph) C(O)(3-CF₃—Ph)2-CF₃-5-thiazolyl 4-CF₃-5-thiazolyl 1-Me-5-CF₃-2-imidazolyl1-Me-4-CF₃-2-imidazolyl C(O)(3,5-diCl—Ph) C(O)(3-(2-Cl-4-CF₃—Ph)Ph) R²is 5-pyrimidinyl Cl F CF₃ Me c-Pr C(O)Me Br C(O)NMe₂ c-Pr-2-(c-Pr)CH═CH₂ C(O)CF₃ CHO I NMe₂ Et C≡CH C(O)Ph CO₂Et cyano NHCHO i-Pr2-thienyl 3-thienyl 4-CF₃-2-thiazolyl 5-CF₃-2-thiazolyl2-CF₃-4-thiazolyl 5-CF₃-4-thiazolyl C(O)(2-F—Ph) C(O)(3-CF₃—Ph)2-CF₃-5-thiazolyl 4-CF₃-5-thiazolyl 1-Me-5-CF₃-2-imidazolyl1-Me-4-CF₃-2-imidazolyl C(O)(3,5-diCl—Ph) C(O)(3-(2-Cl-4-CF₃—Ph)Ph) R²is 2-methyl-5-pyrimdinyl Cl F CF₃ Me c-Pr C(O)Me Br C(O)NMe₂c-Pr-2-(c-Pr) CH═CH₂ C(O)CF₃ CHO I NMe₂ Et C≡CH C(O)Ph CO₂Et cyano NHCHOi-Pr 2-thienyl 3-thienyl 4-CF₃-2-thiazolyl 5-CF₃-2-thiazolyl2-CF₃-4-thiazolyl 5-CF₃-4-thiazolyl C(O)(2-F—Ph) C(O)(3-CF₃—Ph)2-CF₃-5-thiazolyl 4-CF₃-5-thiazolyl 1-Me-5-CF₃-2-imidazolyl1-Me-4-CF₃-2-imidazolyl C(O)(3,5-diCl—Ph) C(O)(3-(2-Cl-4-CF₃—Ph)Ph)

TABLE 29

R¹ Z is a direct bond; R² is 2-chloro-5-thiazolyl CH═CH(Ph)CH═CH(2-Me—Ph) CH═CH(3-CF₃O—Ph) CH═CH(c-Pr-2-(c-Pr)) CH═CH(2-MeO—Ph)CH═CH(3-MeO—Ph) CH═CH(CF₃) CH═CH(2-F—Ph) CH═CH(3-Me—Ph) CH═CH(4-CF₃O—Ph)CH═CH(C(O)Me) CH═CH(3-CF₃—Ph) CH═CH(4-CF₃—Ph) CH═CH(3,5-diCl—Ph)CH═CH(3-F—Ph) CH═CH(4-Me—Ph) CH═CH(Me) CH═CH(CO₂Et) CH═CH(i-Pr)CH═CH(c-Pr) CH═CH(4-F—Ph) CH═CH(2-CF₃—Ph) CH═CH(Et) CH═CH(C(O)NMe₂)CH═CH(4-MeO—Ph) CH═CH(2-CF₃O—Ph) CH═CH(3-(2-Cl-4-CF₃—Ph)Ph) Z is adirect bond; R² is 6-chloro-3-pyridinyl CH═CH(Ph) CH═CH(2-Me—Ph)CH═CH(3-CF₃O—Ph) CH═CH(c-Pr-2-(c-Pr)) CH═CH(2-MeO—Ph) CH═CH(3-MeO—Ph)CH═CH(CF₃) CH═CH(2-F—Ph) CH═CH(3-Me—Ph) CH═CH(4-CF₃O—Ph) CH═CH(C(O)Me)CH═CH(3-CF₃—Ph) CH═CH(4-CF₃—Ph) CH═CH(3,5-diCl—Ph) CH═CH(3-F—Ph)CH═CH(4-Me—Ph) CH═CH(Me) CH═CH(CO₂Et) CH═CH(i-Pr) CH═CH(c-Pr)CH═CH(4-F—Ph) CH═CH(2-CF₃—Ph) CH═CH(Et) CH═CH(C(O)NMe₂) CH═CH(4-MeO—Ph)CH═CH(2-CF₃O—Ph) CH═CH(3-(2-Cl-4-CF₃—Ph)Ph) Z is a direct bond; R² is6-fluoro-3-pyridinyl CH═CH(Ph) CH═CH(2-Me—Ph) CH═CH(3-CF₃O—Ph)CH═CH(c-Pr-2-(c-Pr)) CH═CH(2-MeO—Ph) CH═CH(3-MeO—Ph) CH═CH(CF₃)CH═CH(2-F—Ph) CH═CH(3-Me—Ph) CH═CH(4-CF₃O—Ph) CH═CH(C(O)Me)CH═CH(3-CF₃—Ph) CH═CH(4-CF₃—Ph) CH═CH(3,5-diCl—Ph) CH═CH(3-F—Ph)CH═CH(4-Me—Ph) CH═CH(Me) CH═CH(CO₂Et) CH═CH(i-Pr) CH═CH(c-Pr)CH═CH(4-F—Ph) CH═CH(2-CF₃—Ph) CH═CH(Et) CH═CH(C(O)NMe₂) CH═CH(4-MeO—Ph)CH═CH(2-CF₃O—Ph) CH═CH(3-(2-Cl-4-CF₃—Ph)Ph) Z is a direct bond; R² is5-pyrimidinyl CH═CH(Ph) CH═CH(2-Me—Ph) CH═CH(3-CF₃O—Ph)CH═CH(c-Pr-2-(c-Pr)) CH═CH(2-MeO—Ph) CH═CH(3-MeO—Ph) CH═CH(CF₃)CH═CH(2-F—Ph) CH═CH(3-Me—Ph) CH═CH(4-CF₃O—Ph) CH═CH(C(O)Me)CH═CH(3-CF₃—Ph) CH═CH(4-CF₃—Ph) CH═CH(3,5-diCl—Ph) CH═CH(3-F—Ph)CH═CH(4-Me—Ph) CH═CH(Me) CH═CH(CO₂Et) CH═CH(i-Pr) CH═CH(c-Pr)CH═CH(4-F—Ph) CH═CH(2-CF₃—Ph) CH═CH(Et) CH═CH(C(O)NMe₂) CH═CH(4-MeO—Ph)CH═CH(2-CF₃O—Ph) CH═CH(3-(2-Cl-4-CF₃—Ph)Ph) Z is a direct bond; R² is2-methyl-5-pyrimidinyl CH═CH(Ph) CH═CH(2-Me—Ph) CH═CH(3-CF₃O—Ph)CH═CH(c-Pr-2-(c-Pr)) CH═CH(2-MeO—Ph) CH═CH(3-MeO—Ph) CH═CH(CF₃)CH═CH(2-F—Ph) CH═CH(3-Me—Ph) CH═CH(4-CF₃O—Ph) CH═CH(C(O)Me)CH═CH(3-CF₃—Ph) CH═CH(4-CF₃—Ph) CH═CH(3,5-diCl—Ph) CH═CH(3-F—Ph)CH═CH(4-Me—Ph) CH═CH(Me) CH═CH(CO₂Et) CH═CH(i-Pr) CH═CH(c-Pr)CH═CH(4-F—Ph) CH═CH(2-CF₃—Ph) CH═CH(Et) CH═CH(C(O)NMe₂) CH═CH(4-MeO—Ph)CH═CH(2-CF₃O—Ph) CH═CH(3-(2-Cl-4-CF₃—Ph)Ph) Z is a direct bond; R² is2-chloro-5-thiazolyl CH═CH(Ph) CH═CH(2-Me—Ph) CH═CH(3-CF₃O—Ph)CH═CH(c-Pr-2-(c-Pr)) CH═CH(2-MeO—Ph) CH═CH(3-MeO—Ph) CH═CH(CF₃)CH═CH(2-F—Ph) CH═CH(3-Me—Ph) CH═CH(4-CF₃O—Ph) CH═CH(C(O)Me)CH═CH(3-CF₃—Ph) CH═CH(4-CF₃—Ph) CH═CH(3,5-diCl—Ph) CH═CH(3-F—Ph)CH═CH(4-Me—Ph) CH═CH(Me) CH═CH(CO₂Et) CH═CH(i-Pr) CH═CH(c-Pr)CH═CH(4-F—Ph) CH═CH(2-CF₃—Ph) CH═CH(Et) CH═CH(C(O)NMe₂) CH═CH(4-MeO—Ph)CH═CH(2-CF₃O—Ph) CH═CH(3-(2-Cl-4-CF₃—Ph)Ph) Z is a direct bond; R² is6-chloro-3-pyridinyl CH═CH(Ph) CH═CH(2-Me—Ph) CH═CH(3-CF₃O—Ph)CH═CH(c-Pr-2-(c-Pr)) CH═CH(2-MeO—Ph) CH═CH(3-MeO—Ph) CH═CH(CF₃)CH═CH(2-F—Ph) CH═CH(3-Me—Ph) CH═CH(4-CF₃O—Ph) CH═CH(C(O)Me)CH═CH(3-CF₃—Ph) CH═CH(4-CF₃—Ph) CH═CH(3,5-diCl—Ph) CH═CH(3-F—Ph)CH═CH(4-Me—Ph) CH═CH(Me) CH═CH(CO₂Et) CH═CH(i-Pr) CH═CH(c-Pr)CH═CH(4-F—Ph) CH═CH(2-CF₃—Ph) CH═CH(Et) CH═CH(C(O)NMe₂) CH═CH(4-MeO—Ph)CH═CH(2-CF₃O—Ph) CH═CH(3-(2-Cl-4-CF₃—Ph)Ph) Z is a direct bond; R² is6-fluoro-3-pyridinyl CH═CH(Ph) CH═CH(2-Me—Ph) CH═CH(3-CF₃O—Ph)CH═CH(c-Pr-2-(c-Pr)) CH═CH(2-MeO—Ph) CH═CH(3-MeO—Ph) CH═CH(CF₃)CH═CH(2-F—Ph) CH═CH(3-Me—Ph) CH═CH(4-CF₃O—Ph) CH═CH(C(O)Me)CH═CH(3-CF₃—Ph) CH═CH(4-CF₃—Ph) CH═CH(3,5-diCl—Ph) CH═CH(3-F—Ph)CH═CH(4-Me—Ph) CH═CH(Me) CH═CH(CO₂Et) CH═CH(i-Pr) CH═CH(c-Pr)CH═CH(4-F—Ph) CH═CH(2-CF₃—Ph) CH═CH(Et) CH═CH(C(O)NMe₂) CH═CH(4-MeO—Ph)CH═CH(2-CF₃O—Ph) CH═CH(3-(2-Cl-4-CF₃—Ph)Ph) Z is a direct bond; R² is5-pyrimidinyl CH═CH(Ph) CH═CH(2-Me—Ph) CH═CH(3-CF₃O—Ph)CH═CH(c-Pr-2-(c-Pr)) CH═CH(2-MeO—Ph) CH═CH(3-MeO—Ph) CH═CH(CF₃)CH═CH(2-F—Ph) CH═CH(3-Me—Ph) CH═CH(4-CF₃O—Ph) CH═CH(C(O)Me)CH═CH(3-CF₃—Ph) CH═CH(4-CF₃—Ph) CH═CH(3,5-diCl—Ph) CH═CH(3-F—Ph)CH═CH(4-Me—Ph) CH═CH(Me) CH═CH(CO₂Et) CH═CH(i-Pr) CH═CH(c-Pr)CH═CH(4-F—Ph) CH═CH(2-CF₃—Ph) CH═CH(Et) CH═CH(C(O)NMe₂) CH═CH(4-MeO—Ph)CH═CH(2-CF₃O—Ph) CH═CH(3-(2-Cl-4-CF₃—Ph)Ph) Z is a direct bond; R² is2-methyl-5-pyrimidinyl CH═CH(Ph) CH═CH(2-Me—Ph) CH═CH(3-CF₃O—Ph)CH═CH(c-Pr-2-(c-Pr)) CH═CH(2-MeO—Ph) CH═CH(3-MeO—Ph) CH═CH(CF₃)CH═CH(2-F—Ph) CH═CH(3-Me—Ph) CH═CH(4-CF₃O—Ph) CH═CH(C(O)Me)CH═CH(3-CF₃—Ph) CH═CH(4-CF₃—Ph) CH═CH(3,5-diCl—Ph) CH═CH(3-F—Ph)CH═CH(4-Me—Ph) CH═CH(Me) CH═CH(CO₂Et) CH═CH(i-Pr) CH═CH(c-Pr)CH═CH(4-F—Ph) CH═CH(2-CF₃—Ph) CH═CH(Et) CH═CH(C(O)NMe₂) CH═CH(4-MeO—Ph)CH═CH(2-CF₃O—Ph) CH═CH(3-(2-Cl-4-CF₃—Ph)Ph) Z is O; R² is2-chloro-5-thiazolyl CH═CH(Ph) CH═CH(2-Me—Ph) CH═CH(3-CF₃O—Ph)CH═CH(c-Pr-2-(c-Pr)) CH═CH(2-MeO—Ph) CH═CH(3-MeO—Ph) CH═CH(CF₃)CH═CH(2-F—Ph) CH═CH(3-Me—Ph) CH═CH(4-CF₃O—Ph) CH═CH(C(O)Me)CH═CH(3-CF₃—Ph) CH═CH(4-CF₃—Ph) CH═CH(3,5-diCl—Ph) CH═CH(3-F—Ph)CH═CH(4-Me—Ph) CH═CH(Me) CH═CH(CO₂Et) CH═CH(i-Pr) CH═CH(c-Pr)CH═CH(4-F—Ph) CH═CH(2-CF₃—Ph) CH═CH(Et) CH═CH(C(O)NMe₂) CH═CH(4-MeO—Ph)CH═CH(2-CF₃O—Ph) CH═CH(3-(2-Cl-4-CF₃—Ph)Ph) Z is O; R² is6-chloro-3-pyridinyl CH═CH(Ph) CH═CH(2-Me—Ph) CH═CH(3-CF₃O—Ph)CH═CH(c-Pr-2-(c-Pr)) CH═CH(2-MeO—Ph) CH═CH(3-MeO—Ph) CH═CH(CF₃)CH═CH(2-F—Ph) CH═CH(3-Me—Ph) CH═CH(4-CF₃O—Ph) CH═CH(C(O)Me)CH═CH(3-CF₃—Ph) CH═CH(4-CF₃—Ph) CH═CH(3,5-diCl—Ph) CH═CH(3-F—Ph)CH═CH(4-Me—Ph) CH═CH(Me) CH═CH(CO₂Et) CH═CH(i-Pr) CH═CH(c-Pr)CH═CH(4-F—Ph) CH═CH(2-CF₃—Ph) CH═CH(Et) CH═CH(C(O)NMe₂) CH═CH(4-MeO—Ph)CH═CH(2-CF₃O—Ph) CH═CH(3-(2-Cl-4-CF₃—Ph)Ph) Z is O; R² is6-fluoro-3-pyridinyl CH═CH(Ph) CH═CH(2-Me—Ph) CH═CH(3-CF₃O—Ph)CH═CH(c-Pr-2-(c-Pr)) CH═CH(2-MeO—Ph) CH═CH(3-MeO—Ph) CH═CH(CF₃)CH═CH(2-F—Ph) CH═CH(3-Me—Ph) CH═CH(4-CF₃O—Ph) CH═CH(C(O)Me)CH═CH(3-CF₃—Ph) CH═CH(4-CF₃—Ph) CH═CH(3,5-diCl—Ph) CH═CH(3-F—Ph)CH═CH(4-Me—Ph) CH═CH(Me) CH═CH(CO₂Et) CH═CH(i-Pr) CH═CH(c-Pr)CH═CH(4-F—Ph) CH═CH(2-CF₃—Ph) CH═CH(Et) CH═CH(C(O)NMe₂) CH═CH(4-MeO—Ph)CH═CH(2-CF₃O—Ph) CH═CH(3-(2-Cl-4-CF₃—Ph)Ph) Z is O; R² is 5-pyrimidinylCH═CH(Ph) CH═CH(2-Me—Ph) CH═CH(3-CF₃O—Ph) CH═CH(c-Pr-2-(c-Pr))CH═CH(2-MeO—Ph) CH═CH(3-MeO—Ph) CH═CH(CF₃) CH═CH(2-F—Ph) CH═CH(3-Me—Ph)CH═CH(4-CF₃O—Ph) CH═CH(C(O)Me) CH═CH(3-CF₃—Ph) CH═CH(4-CF₃—Ph)CH═CH(3,5-diCl—Ph) CH═CH(3-F—Ph) CH═CH(4-Me—Ph) CH═CH(Me) CH═CH(CO₂Et)CH═CH(i-Pr) CH═CH(c-Pr) CH═CH(4-F—Ph) CH═CH(2-CF₃—Ph) CH═CH(Et)CH═CH(C(O)NMe₂) CH═CH(4-MeO—Ph) CH═CH(2-CF₃O—Ph)CH═CH(3-(2-Cl-4-CF₃—Ph)Ph) Z is O; R² is 2-methyl-5-pyrimidinylCH═CH(Ph) CH═CH(2-Me—Ph) CH═CH(3-CF₃O—Ph) CH═CH(c-Pr-2-(c-Pr))CH═CH(2-MeO—Ph) CH═CH(3-MeO—Ph) CH═CH(CF₃) CH═CH(2-F—Ph) CH═CH(3-Me—Ph)CH═CH(4-CF₃O—Ph) CH═CH(C(O)Me) CH═CH(3-CF₃—Ph) CH═CH(4-CF₃—Ph)CH═CH(3,5-diCl—Ph) CH═CH(3-F—Ph) CH═CH(4-Me—Ph) CH═CH(Me) CH═CH(CO₂Et)CH═CH(i-Pr) CH═CH(c-Pr) CH═CH(4-F—Ph) CH═CH(2-CF₃—Ph) CH═CH(Et)CH═CH(C(O)NMe₂) CH═CH(4-MeO—Ph) CH═CH(2-CF₃O—Ph)CH═CH(3-(2-Cl-4-CF₃—Ph)Ph) Z is NMe; R² is 2-chloro-5-thiaolyl CH═CH(Ph)CH═CH(2-Me—Ph) CH═CH(3-CF₃O—Ph) CH═CH(c-Pr-2-(c-Pr)) CH═CH(2-MeO—Ph)CH═CH(3-MeO—Ph) CH═CH(CF₃) CH═CH(2-F—Ph) CH═CH(3-Me—Ph) CH═CH(4-CF₃O—Ph)CH═CH(C(O)Me) CH═CH(3-CF₃—Ph) CH═CH(4-CF₃—Ph) CH═CH(3,5-diCl—Ph)CH═CH(3-F—Ph) CH═CH(4-Me—Ph) CH═CH(Me) CH═CH(CO₂Et) CH═CH(i-Pr)CH═CH(c-Pr) CH═CH(4-F—Ph) CH═CH(2-CF₃—Ph) CH═CH(Et) CH═CH(C(O)NMe₂)CH═CH(4-MeO—Ph) CH═CH(2-CF₃O—Ph) CH═CH(3-(2-Cl-4-CF₃—Ph)Ph) Z is NMe; R²is 6-chloro-3-pyridinyl CH═CH(Ph) CH═CH(2-Me—Ph) CH═CH(3-CF₃O—Ph)CH═CH(c-Pr-2-(c-Pr)) CH═CH(2-MeO—Ph) CH═CH(3-MeO—Ph) CH═CH(CF₃)CH═CH(2-F—Ph) CH═CH(3-Me—Ph) CH═CH(4-CF₃O—Ph) CH═CH(C(O)Me)CH═CH(3-CF₃—Ph) CH═CH(4-CF₃—Ph) CH═CH(3,5-diCl—Ph) CH═CH(3-F—Ph)CH═CH(4-Me—Ph) CH═CH(Me) CH═CH(CO₂Et) CH═CH(i-Pr) CH═CH(c-Pr)CH═CH(4-F—Ph) CH═CH(2-CF₃—Ph) CH═CH(Et) CH═CH(C(O)NMe₂) CH═CH(4-MeO—Ph)CH═CH(2-CF₃O—Ph) CH═CH(3-(2-Cl-4-CF₃—Ph)Ph) Z is NMe; R² is6-fluoro-3-pyridinyl CH═CH(Ph) CH═CH(2-Me—Ph) CH═CH(3-CF₃O—Ph)CH═CH(c-Pr-2-(c-Pr)) CH═CH(2-MeO—Ph) CH═CH(3-MeO—Ph) CH═CH(CF₃)CH═CH(2-F—Ph) CH═CH(3-Me—Ph) CH═CH(4-CF₃O—Ph) CH═CH(C(O)Me)CH═CH(3-CF₃—Ph) CH═CH(4-CF₃—Ph) CH═CH(3,5-diCl—Ph) CH═CH(3-F—Ph)CH═CH(4-Me—Ph) CH═CH(Me) CH═CH(CO₂Et) CH═CH(i-Pr) CH═CH(c-Pr)CH═CH(4-F—Ph) CH═CH(2-CF₃—Ph) CH═CH(Et) CH═CH(C(O)NMe₂) CH═CH(4-MeO—Ph)CH═CH(2-CF₃O—Ph) CH═CH(3-(2-Cl-4-CF₃—Ph)Ph) Z is NMe; R² is5-pyrimidinyl CH═CH(Ph) CH═CH(2-Me—Ph) CH═CH(3-CF₃O—Ph)CH═CH(c-Pr-2-(c-Pr)) CH═CH(2-MeO—Ph) CH═CH(3-MeO—Ph) CH═CH(CF₃)CH═CH(2-F—Ph) CH═CH(3-Me—Ph) CH═CH(4-CF₃O—Ph) CH═CH(C(O)Me)CH═CH(3-CF₃—Ph) CH═CH(4-CF₃—Ph) CH═CH(3,5-diCl—Ph) CH═CH(3-F—Ph)CH═CH(4-Me—Ph) CH═CH(Me) CH═CH(CO₂Et) CH═CH(i-Pr) CH═CH(c-Pr)CH═CH(4-F—Ph) CH═CH(2-CF₃—Ph) CH═CH(Et) CH═CH(C(O)NMe₂) CH═CH(4-MeO—Ph)CH═CH(2-CF₃O—Ph) CH═CH(3-(2-Cl-4-CF₃—Ph)Ph) Z is NMe; R² is2-methyl-5-pyrimidinyl CH═CH(Ph) CH═CH(2-Me—Ph) CH═CH(3-CF₃O—Ph)CH═CH(c-Pr-2-(c-Pr)) CH═CH(2-MeO—Ph) CH═CH(3-MeO—Ph) CH═CH(CF₃)CH═CH(2-F—Ph) CH═CH(3-Me—Ph) CH═CH(4-CF₃O—Ph) CH═CH(C(O)Me)CH═CH(3-CF₃—Ph) CH═CH(4-CF₃—Ph) CH═CH(3,5-diCl—Ph) CH═CH(3-F—Ph)CH═CH(4-Me—Ph) CH═CH(Me) CH═CH(CO₂Et) CH═CH(i-Pr) CH═CH(c-Pr)CH═CH(4-F—Ph) CH═CH(2-CF₃—Ph) CH═CH(Et) CH═CH(C(O)NMe₂) CH═CH(4-MeO—Ph)CH═CH(2-CF₃O—Ph) CH═CH(3-(2-Cl-4-CF₃—Ph)Ph) Z is C(O); R² is2-chloro-5-thiaolyl CH═CH(Ph) CH═CH(2-Me—Ph) CH═CH(3-CF₃O—Ph)CH═CH(c-Pr-2-(c-Pr)) CH═CH(2-MeO—Ph) CH═CH(3-MeO—Ph) CH═CH(CF₃)CH═CH(2-F—Ph) CH═CH(3-Me—Ph) CH═CH(4-CF₃O—Ph) CH═CH(C(O)Me)CH═CH(3-CF₃—Ph) CH═CH(4-CF₃—Ph) CH═CH(3,5-diCl—Ph) CH═CH(3-F—Ph)CH═CH(4-Me—Ph) CH═CH(Me) CH═CH(CO₂Et) CH═CH(i-Pr) CH═CH(c-Pr)CH═CH(4-F—Ph) CH═CH(2-CF₃—Ph) CH═CH(Et) CH═CH(C(O)NMe₂) CH═CH(4-MeO—Ph)CH═CH(2-CF₃O—Ph) CH═CH(3-(2-Cl-4-CF₃—Ph)Ph) Z is C(O); R² is6-chloro-3-pyridinyl CH═CH(Ph) CH═CH(2-Me—Ph) CH═CH(3-CF₃O—Ph)CH═CH(c-Pr-2-(c-Pr)) CH═CH(2-MeO—Ph) CH═CH(3-MeO—Ph) CH═CH(CF₃)CH═CH(2-F—Ph) CH═CH(3-Me—Ph) CH═CH(4-CF₃O—Ph) CH═CH(C(O)Me)CH═CH(3-CF₃—Ph) CH═CH(4-CF₃—Ph) CH═CH(3,5-diCl—Ph) CH═CH(3-F—Ph)CH═CH(4-Me—Ph) CH═CH(Me) CH═CH(CO₂Et) CH═CH(i-Pr) CH═CH(c-Pr)CH═CH(4-F—Ph) CH═CH(2-CF₃—Ph) CH═CH(Et) CH═CH(C(O)NMe₂) CH═CH(4-MeO—Ph)CH═CH(2-CF₃O—Ph) CH═CH(3-(2-Cl-4-CF₃—Ph)Ph) Z is C(O); R² is6-fluoro-3-pyrimidinyl CH═CH(Ph) CH═CH(2-Me—Ph) CH═CH(3-CF₃O—Ph)CH═CH(c-Pr-2-(c-Pr)) CH═CH(2-MeO—Ph) CH═CH(3-MeO—Ph) CH═CH(CF₃)CH═CH(2-F—Ph) CH═CH(3-Me—Ph) CH═CH(4-CF₃O—Ph) CH═CH(C(O)Me)CH═CH(3-CF₃—Ph) CH═CH(4-CF₃—Ph) CH═CH(3,5-diCl—Ph) CH═CH(3-F—Ph)CH═CH(4-Me—Ph) CH═CH(Me) CH═CH(CO₂Et) CH═CH(i-Pr) CH═CH(c-Pr)CH═CH(4-F—Ph) CH═CH(2-CF₃—Ph) CH═CH(Et) CH═CH(C(O)NMe₂) CH═CH(4-MeO—Ph)CH═CH(2-CF₃O—Ph) CH═CH(3-(2-Cl-4-CF₃—Ph)Ph) Z is C(O); R² is5-pyrimidinyl CH═CH(Ph) CH═CH(2-Me—Ph) CH═CH(3-CF₃O—Ph)CH═CH(c-Pr-2-(c-Pr)) CH═CH(2-MeO—Ph) CH═CH(3-MeO—Ph) CH═CH(CF₃)CH═CH(2-F—Ph) CH═CH(3-Me—Ph) CH═CH(4-CF₃O—Ph) CH═CH(C(O)Me)CH═CH(3-CF₃—Ph) CH═CH(4-CF₃—Ph) CH═CH(3,5-diCl—Ph) CH═CH(3-F—Ph)CH═CH(4-Me—Ph) CH═CH(Me) CH═CH(CO₂Et) CH═CH(i-Pr) CH═CH(c-Pr)CH═CH(4-F—Ph) CH═CH(2-CF₃—Ph) CH═CH(Et) CH═CH(C(O)NMe₂) CH═CH(4-MeO—Ph)CH═CH(2-CF₃O—Ph) CH═CH(3-(2-Cl-4-CF₃—Ph)Ph) Z is C(O); R² is2-methyl-5-pyrimidinyl CH═CH(Ph) CH═CH(2-Me—Ph) CH═CH(3-CF₃O—Ph)CH═CH(c-Pr-2-(c-Pr)) CH═CH(2-MeO—Ph) CH═CH(3-MeO—Ph) CH═CH(CF₃)CH═CH(2-F—Ph) CH═CH(3-Me—Ph) CH═CH(4-CF₃O—Ph) CH═CH(C(O)Me)CH═CH(3-CF₃—Ph) CH═CH(4-CF₃—Ph) CH═CH(3,5-diCl—Ph) CH═CH(3-F—Ph)CH═CH(4-Me—Ph) CH═CH(Me) CH═CH(CO₂Et) CH═CH(i-Pr) CH═CH(c-Pr)CH═CH(4-F—Ph) CH═CH(2-CF₃—Ph) CH═CH(Et) CH═CH(C(O)NMe₂) CH═CH(4-MeO—Ph)CH═CH(2-CF₃O—Ph) CH═CH(3-(2-Cl-4-CF₃—Ph)Ph) Z is C(O)NMe; R² is2-chloro-5-thiazolyl CH═CH(Ph) CH═CH(2-Me—Ph) CH═CH(3-CF₃O—Ph)CH═CH(c-Pr-2-(c-Pr)) CH═CH(2-MeO—Ph) CH═CH(3-MeO—Ph) CH═CH(CF₃)CH═CH(2-F—Ph) CH═CH(3-Me—Ph) CH═CH(4-CF₃O—Ph) CH═CH(C(O)Me)CH═CH(3-CF₃—Ph) CH═CH(4-CF₃—Ph) CH═CH(3,5-diCl—Ph) CH═CH(3-F—Ph)CH═CH(4-Me—Ph) CH═CH(Me) CH═CH(CO₂Et) CH═CH(i-Pr) CH═CH(c-Pr)CH═CH(4-F—Ph) CH═CH(2-CF₃—Ph) CH═CH(Et) CH═CH(C(O)NMe₂) CH═CH(4-MeO—Ph)CH═CH(2-CF₃O—Ph) CH═CH(3-(2-Cl-4-CF₃—Ph)Ph) Z is C(O)NMe; R² is6-chloro-3-pyridinyl CH═CH(Ph) CH═CH(2-Me—Ph) CH═CH(3-CF₃O—Ph)CH═CH(c-Pr-2-(c-Pr)) CH═CH(2-MeO—Ph) CH═CH(3-MeO—Ph) CH═CH(CF₃)CH═CH(2-F—Ph) CH═CH(3-Me—Ph) CH═CH(4-CF₃O—Ph) CH═CH(C(O)Me)CH═CH(3-CF₃—Ph) CH═CH(4-CF₃—Ph) CH═CH(3,5-diCl—Ph) CH═CH(3-F—Ph)CH═CH(4-Me—Ph) CH═CH(Me) CH═CH(CO₂Et) CH═CH(i-Pr) CH═CH(c-Pr)CH═CH(4-F—Ph) CH═CH(2-CF₃—Ph) CH═CH(Et) CH═CH(C(O)NMe₂) CH═CH(4-MeO—Ph)CH═CH(2-CF₃O—Ph) CH═CH(3-(2-Cl-4-CF₃—Ph)Ph) Z is C(O)NMe; R² is6-fluoro-3-pyridinyl CH═CH(Ph) CH═CH(2-Me—Ph) CH═CH(3-CF₃O—Ph)CH═CH(c-Pr-2-(c-Pr)) CH═CH(2-MeO—Ph) CH═CH(3-MeO—Ph) CH═CH(CF₃)CH═CH(2-F—Ph) CH═CH(3-Me—Ph) CH═CH(4-CF₃O—Ph) CH═CH(C(O)Me)CH═CH(3-CF₃—Ph) CH═CH(4-CF₃—Ph) CH═CH(3,5-diCl—Ph) CH═CH(3-F—Ph)CH═CH(4-Me—Ph) CH═CH(Me) CH═CH(CO₂Et) CH═CH(i-Pr) CH═CH(c-Pr)CH═CH(4-F—Ph) CH═CH(2-CF₃—Ph) CH═CH(Et) CH═CH(C(O)NMe₂) CH═CH(4-MeO—Ph)CH═CH(2-CF₃O—Ph) CH═CH(3-(2-Cl-4-CF₃—Ph)Ph) Z is C(O)NMe; R² is5-pyrimidinyl CH═CH(Ph) CH═CH(2-Me—Ph) CH═CH(3-CF₃O—Ph)CH═CH(c-Pr-2-(c-Pr)) CH═CH(2-MeO—Ph) CH═CH(3-MeO—Ph) CH═CH(CF₃)CH═CH(2-F—Ph) CH═CH(3-Me—Ph) CH═CH(4-CF₃O—Ph) CH═CH(C(O)Me)CH═CH(3-CF₃—Ph) CH═CH(4-CF₃—Ph) CH═CH(3,5-diCl—Ph) CH═CH(3-F—Ph)CH═CH(4-Me—Ph) CH═CH(Me) CH═CH(CO₂Et) CH═CH(i-Pr) CH═CH(c-Pr)CH═CH(4-F—Ph) CH═CH(2-CF₃—Ph) CH═CH(Et) CH═CH(C(O)NMe₂) CH═CH(4-MeO—Ph)CH═CH(2-CF₃O—Ph) CH═CH(3-(2-Cl-4-CF₃—Ph)Ph) Z is C(O)NMe; R² is2-methyl-5-pyrimidinyl CH═CH(Ph) CH═CH(2-Me—Ph) CH═CH(3-CF₃O—Ph)CH═CH(c-Pr-2-(c-Pr)) CH═CH(2-MeO—Ph) CH═CH(3-MeO—Ph) CH═CH(CF₃)CH═CH(2-F—Ph) CH═CH(3-Me—Ph) CH═CH(4-CF₃O—Ph) CH═CH(C(O)Me)CH═CH(3-CF₃—Ph) CH═CH(4-CF₃—Ph) CH═CH(3,5-diCl—Ph) CH═CH(3-F—Ph)CH═CH(4-Me—Ph) CH═CH(Me) CH═CH(CO₂Et) CH═CH(i-Pr) CH═CH(c-Pr)CH═CH(4-F—Ph) CH═CH(2-CF₃—Ph) CH═CH(Et) CH═CH(C(O)NMe₂) CH═CH(4-MeO—Ph)CH═CH(2-CF₃O—Ph) CH═CH(3-(2-Cl-4-CF₃—Ph)Ph)

TABLE 30

R R² is 2-chloro-5-thiazolyl Br I Me Et c-Pr Ph CH₂F CHF₂ OMe OEt O-n-PrOPh O-i-Pr OCH₂CH═CH₂ OCH₂≡CCH O-c-Pr OCHF₂ SCF₃ SCF₃ SCHF₂ S(O)CF₃SO₂CF₃ CO₂Me CO₂Et C(O)NHMe C(O)NMe₂ C(═NOMe)Me CH≡CH₂ CCH 3-ClPh6-Cl-3-pyridinyl 6-F-3-pyridinyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl 4-CF₃-2-thiazolyl1-Me-4-CF₃-2-imidazolyl R² is 6-chloro-3-pyridinyl Br I Me Et c-Pr PhCH₂F CHF₂ OMe OEt O-n-Pr OPh O-i-Pr OCH₂CH═CH₂ OCH₂≡CCH O-c-Pr OCHF₂SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Et C(O)NHMe C(O)NMe₂ C(═NOMe)MeCH≡CH₂ CCH 3-ClPh 6-Cl-3-pyridinyl 6-F-3-pyridinyl N-Me-4-pyrazolyl3-Me-5-isoxazolyl 6-(6-Cl-3-pyridinyl)-3-pyridinyl 4-CF₃-2-thiazolyl1-Me-4-CF₃-2-imidazolyl R² is 6-fluoro-3-pyridinyl Br I Me Et c-Pr PhCH₂F CHF₂ OMe OEt O-n-Pr OPh O-i-Pr OCH₂CH═CH₂ OCH₂≡CCH O-c-Pr OCHF₂SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Et C(O)NHMe C(O)NMe₂ C(═NOMe)MeCH≡CH₂ CCH 3-ClPh 6-Cl-3-pyridinyl 6-F-3-pyridinyl N-Me-4-pyrazolyl3-Me-5-isoxazolyl 6-(6-Cl-3-pyridinyl)-3-pyridinyl 4-CF₃-2-thiazolyl1-Me-4-CF₃-2-imidazolyl R² is 5-pyrimidinyl Br I Me Et c-Pr Ph CH₂F CHF₂OMe OEt O-n-Pr OPh O-i-Pr OCH₂CH═CH₂ OCH₂≡CCH O-c-Pr OCHF₂ SCF₃ SCF₃SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Et C(O)NHMe C(O)NMe₂ C(═NOMe)Me CH≡CH₂ CCH3-ClPh 6-Cl-3-pyridinyl 6-F-3-pyridinyl N-Me-4-pyrazolyl3-Me-5-isoxazolyl 6-(6-Cl-3-pyridinyl)-3-pyridinyl 4-CF₃-2-thiazolyl1-Me-4-CF₃-2-imidazolyl R² is 2-methyl-5-pyrimidinyl Br I Me Et c-Pr PhCH₂F CHF₂ OMe OEt O-n-Pr OPh O-i-Pr OCH₂CH═CH₂ OCH₂≡CCH O-c-Pr OCHF₂SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Et C(O)NHMe C(O)NMe₂ C(═NOMe)MeCH≡CH₂ CCH 3-ClPh 6-Cl-3-pyridinyl 6-F-3-pyridinyl N-Me-4-pyrazolyl3-Me-5-isoxazolyl 6-(6-Cl-3-pyridinyl)-3-pyridinyl 4-CF₃-2-thiazolyl1-Me-4-CF₃-2-imidazolyl

TABLE 31

R R² is 2-chloro-5-thiazolyl H F Cl Br I Me Et c-Pr CF₃ CH₂F CHF₂ OMeOEt O-n-Pr O-i-Pr OCH₂CH═CH₂ OCH₂C≡CH O-c-Pr OCF₃ OCHF₂ SCF₃ SCF₃ SCHF₂S(O)CF₃ SO₂CF₃ CO₂Me CO₂Et cyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me CH═CH₂C≡CH Ph OPh 3-ClPh 6-Cl-3-pyridinyl 6-F-3-pyridinyl N-Me-4-pyrazolyl3-Me-5-isoxazolyl 6-(6-Cl-3-pyridinyl)-3-pyridinyl 4-CF₃-2-thiazolyl1-Me-4-CF₃-2-imidazolyl R² is 6-chloro-3-pyridinyl H F Cl Br I Me Etc-Pr CF₃ CH₂F CHF₂ OMe OEt O-n-Pr O-i-Pr OCH₂CH═CH₂ OCH₂C≡CH O-c-Pr OCF₃OCHF₂ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Et cyano C(O)NHMe C(O)NMe₂C(═NOMe)Me CH═CH₂ C≡CH Ph OPh 3-ClPh 6-Cl-3-pyridinyl 6-F-3-pyridinylN-Me-4-pyrazolyl 3-Me-5-isoxazolyl 6-(6-Cl-3-pyridinyl)-3-pyridinyl4-CF₃-2-thiazolyl 1-Me-4-CF₃-2-imidazolyl R² is 6-fluoro-3-pyridinyl H FCl Br I Me Et c-Pr CF₃ CH₂F CHF₂ OMe OEt O-n-Pr O-i-Pr OCH₂CH═CH₂OCH₂C≡CH O-c-Pr OCF₃ OCHF₂ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Etcyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me CH═CH₂ C≡CH Ph OPh 3-ClPh6-Cl-3-pyridinyl 6-F-3-pyridinyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl 4-CF₃-2-thiazolyl1-Me-4-CF₃-2-imidazolyl R² is 5-pyrimidinyl H F Cl Br I Me Et c-Pr CF₃CH₂F CHF₂ OMe OEt O-n-Pr O-i-Pr OCH₂CH═CH₂ OCH₂C≡CH O-c-Pr OCF₃ OCHF₂SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Et cyano C(O)NHMe C(O)NMe₂C(═NOMe)Me CH═CH₂ C≡CH Ph OPh 3-ClPh 6-Cl-3-pyridinyl 6-F-3-pyridinylN-Me-4-pyrazolyl 3-Me-5-isoxazolyl 6-(6-Cl-3-pyridinyl)-3-pyridinyl4-CF₃-2-thiazolyl 1-Me-4-CF₃-2-imidazolyl R² is 2-methyl-5-pyrimidinyl HF Cl Br I Me Et c-Pr CF₃ CH₂F CHF₂ OMe OEt O-n-Pr O-i-Pr OCH₂CH═CH₂OCH₂C≡CH O-c-Pr OCF₃ OCHF₂ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Etcyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me CH═CH₂ C≡CH Ph OPh 3-ClPh6-Cl-3-pyridinyl 6-F-3-pyridinyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl 4-CF₃-2-thiazolyl1-Me-4-CF₃-2-imidazolyl

TABLE 32

R R² is 2-chloro-5-thiazolyl H F Cl Br I Me Et c-Pr CF₃ CH₂F CHF₂ OMeOEt O-n-Pr O-i-Pr OCH₂CH═CH₂ OCH₂C≡CH O-c-Pr OCF₃ OCHF₂ SCF₃ SCF₃ SCHF₂S(O)CF₃ SO₂CF₃ CO₂Me CO₂Et cyano C(O)NHMe C(O)NMe₂ C(═NOMe)Me CH═CH₂C≡CH Ph OPh 3-ClPh 6-Cl-3-pyridinyl 6-F-3-pyridinyl N-Me-4-pyrazolyl3-Me-5-isoxazolyl 6-(6-Cl-3-pyridinyl)-3-pyridinyl 4-CF₃-2-thiazolyl1-Me-4-CF₃-2-imidazolyl R² is 6-chloro-3-pyridinyl H F Cl Br I Me Etc-Pr CF₃ CH₂F CHF₂ OMe OEt O-n-Pr O-i-Pr OCH₂CH═CH₂ OCH₂C≡CH O-c-Pr OCF₃OCHF₂ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Et cyano C(O)NHMe C(O)NMe₂C(═NOMe)Me CH═CH₂ C≡CH Ph OPh 3-ClPh 6-Cl-3-pyridinyl 6-F-3-pyridinylN-Me-4-pyrazolyl 3-Me-5-isoxazolyl 6-(6-Cl-3-pyridinyl)-3-pyridinyl4-CF₃-2-thiazolyl 1-Me-4-CF₃-2-imidazolyl H F Cl Br I Me Et c-Pr CF₃CH₂F CHF₂ OMe OEt O-n-Pr O-i-Pr OCH₂CH═CH₂ OCH₂C≡CH O-c-Pr OCF₃ OCHF₂SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Et cyano C(O)NHMe C(O)NMe₂C(═NOMe)Me CH═CH₂ C≡CH Ph OPh 3-ClPh 6-Cl-3-pyridinyl 6-F-3-pyridinylN-Me-4-pyrazolyl 3-Me-5-isoxazolyl 6-(6-Cl-3-pyridinyl)-3-pyridinyl4-CF₃-2-thiazolyl 1-Me-4-CF₃-2-imidazolyl R² is 5-pyrimidinyl H F Cl BrI Me Et c-Pr CF₃ CH₂F CHF₂ OMe OEt O-n-Pr O-i-Pr OCH₂CH═CH₂ OCH₂C≡CHO-c-Pr OCF₃ OCHF₂ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Et cyanoC(O)NHMe C(O)NMe₂ C(═NOMe)Me CH═CH₂ C≡CH Ph OPh 3-ClPh 6-Cl-3-pyridinyl6-F-3-pyridinyl N-Me-4-pyrazolyl 3-Me-5-isoxazolyl6-(6-Cl-3-pyridinyl)-3-pyridinyl 4-CF₃-2-thiazolyl1-Me-4-CF₃-2-imidazolyl R² is 2-methyl-5-pyrimidinyl H F Cl Br I Me Etc-Pr CF₃ CH₂F CHF₂ OMe OEt O-n-Pr O-i-Pr OCH₂CH═CH₂ OCH₂C≡CH O-c-Pr OCF₃OCHF₂ SCF₃ SCF₃ SCHF₂ S(O)CF₃ SO₂CF₃ CO₂Me CO₂Et cyano C(O)NHMe C(O)NMe₂C(═NOMe)Me CH═CH₂ C≡CH Ph OPh 3-ClPh 6-Cl-3-pyridinyl 6-F-3-pyridinylN-Me-4-pyrazolyl 3-Me-5-isoxazolyl 6-(6-Cl-3-pyridinyl)-3-pyridinyl4-CF₃-2-thiazolyl 1-Me-4-CF₃-2-imidazolyl

A compound of this invention will generally be used as an invertebratepest control active ingredient in a composition, i.e. formulation, withat least one additional component selected from the group consisting ofsurfactants, solid diluents and liquid diluents, which serves as acarrier. The formulation or composition ingredients are selected to beconsistent with the physical properties of the active ingredient, modeof application and environmental factors such as soil type, moisture andtemperature.

Useful formulations include both liquid and solid compositions. Liquidcompositions include solutions (including emulsifiable concentrates),suspensions, emulsions (including microemulsions and/or suspoemulsions)and the like, which optionally can be thickened into gels. The generaltypes of aqueous liquid compositions are soluble concentrate, suspensionconcentrate, capsule suspension, concentrated emulsion, microemulsionand suspo-emulsion. The general types of nonaqueous liquid compositionsare emulsifiable concentrate, microemulsifiable concentrate, dispersibleconcentrate and oil dispersion.

The general types of solid compositions are dusts, powders, granules,pellets, prills, pastilles, tablets, filled films (including seedcoatings) and the like, which can be water-dispersible (“wettable”) orwater-soluble. Films and coatings formed from film-forming solutions orflowable suspensions are particularly useful for seed treatment. Activeingredient can be (micro)encapsulated and further formed into asuspension or solid formulation; alternatively the entire formulation ofactive ingredient can be encapsulated (or “overcoated”). Encapsulationcan control or delay release of the active ingredient. An emulsifiablegranule combines the advantages of both an emulsifiable concentrateformulation and a dry granular formulation. High-strength compositionsare primarily used as intermediates for further formulation.

Sprayable formulations are typically extended in a suitable mediumbefore spraying. Such liquid and solid formulations are formulated to bereadily diluted in the spray medium, usually water. Spray volumes canrange from about one to several thousand liters per hectare, but moretypically are in the range from about ten to several hundred liters perhectare. Sprayable formulations can be tank mixed with water or anothersuitable medium for foliar treatment by aerial or ground application, orfor application to the growing medium of the plant. Liquid and dryformulations can be metered directly into drip irrigation systems ormetered into the furrow during planting. Liquid and solid formulationscan be applied onto seeds of crops and other desirable vegetation asseed treatments before planting to protect developing roots and othersubterranean plant parts and/or foliage through systemic uptake.

The formulations will typically contain effective amounts of activeingredient, diluent and surfactant within the following approximateranges which add up to 100 percent by weight.

Weight Percent Active Ingredient Diluent Surfactant Water-Dispersibleand Water- 0.001-90 0-99.999 0-15 soluble Granules, Tablets and PowdersOil Dispersions, Suspensions,    1-50 40-99    0-50 Emulsions, Solutions(including Emulsifiable Concentrates) Dusts    1-25 70-99    0-5 Granules and Pellets 0.001-95 5-99.999 0-15 High Strength Compositions  90-99 0-10    0-2 

Solid diluents include, for example, clays such as bentonite,montmorillonite, attapulgite and kaolin, gypsum, cellulose, titaniumdioxide, zinc oxide, starch, dextrin, sugars (e.g., lactose, sucrose),silica, talc, mica, diatomaceous earth, urea, calcium carbonate, sodiumcarbonate and bicarbonate, and sodium sulfate. Typical solid diluentsare described in Watkins et al., Handbook of Insecticide Dust Diluentsand Carriers, 2nd Ed., Dorland Books, Caldwell, N.J.

Liquid diluents include, for example, water, N,N-dimethylalkanamides(e.g., N,N-dimethylformamide), limonene, dimethyl sulfoxide,N-alkylpyrrolidones (e.g., N-methylpyrrolidinone), ethylene glycol,triethylene glycol, propylene glycol, dipropylene glycol, polypropyleneglycol, propylene carbonate, butylene carbonate, paraffins (e.g., whitemineral oils, normal paraffins, isoparaffins), alkylbenzenes,alkylnaphthalenes, glycerine, glycerol triacetate, sorbitol, triacetin,aromatic hydrocarbons, dearomatized aliphatics, alkylbenzenes,alkylnaphthalenes, ketones such as cyclohexanone, 2-heptanone,isophorone and 4-hydroxy-4-methyl-2-pentanone, acetates such as isoamylacetate, hexyl acetate, heptyl acetate, octyl acetate, nonyl acetate,tridecyl acetate and isobornyl acetate, other esters such as alkylatedlactate esters, dibasic esters and γ-butyrolactone, and alcohols, whichcan be linear, branched, saturated or unsaturated, such as methanol,ethanol, n-propanol, isopropyl alcohol, n-butanol, isobutyl alcohol,n-hexanol, 2-ethylhexanol, n-octanol, decanol, isodecyl alcohol,isooctadecanol, cetyl alcohol, lauryl alcohol, tridecyl alcohol, oleylalcohol, cyclohexanol, tetrahydrofurfuryl alcohol, diacetone alcohol andbenzyl alcohol. Liquid diluents also include glycerol esters ofsaturated and unsaturated fatty acids (typically C₆-C₂₂), such as plantseed and fruit oils (e.g, oils of olive, castor, linseed, sesame, corn(maize), peanut, sunflower, grapeseed, safflower, cottonseed, soybean,rapeseed, coconut and palm kernel), animal-sourced fats (e.g., beeftallow, pork tallow, lard, cod liver oil, fish oil), and mixturesthereof. Liquid diluents also include alkylated fatty acids (e.g.,methylated, ethylated, butylated) wherein the fatty acids can beobtained by hydrolysis of glycerol esters from plant and animal sources,and can be purified by distillation. Typical liquid diluents aredescribed in Marsden, Solvents Guide, 2nd Ed., Interscience, New York,1950.

The solid and liquid compositions of the present invention often includeone or more surfactants. When added to a liquid, surfactants (also knownas “surface-active agents”) generally modify, most often reduce, thesurface tension of the liquid. Depending on the nature of thehydrophilic and lipophilic groups in a surfactant molecule, surfactantscan be useful as wetting agents, dispersants, emulsifiers or defoamingagents.

Surfactants can be classified as nonionic, anionic or cationic. Nonionicsurfactants useful for the present compositions include, but are notlimited to: alcohol alkoxylates such as alcohol alkoxylates based onnatural and synthetic alcohols (which are branched or linear) andprepared from the alcohols and ethylene oxide, propylene oxide, butyleneoxide or mixtures thereof; amine ethoxylates, alkanolamides andethoxylated alkanolamides; alkoxylated triglycerides such as ethoxylatedsoybean, castor and rapeseed oils; alkylphenol alkoxylates such asoctylphenol ethoxylates, nonylphenol ethoxylates, dinonyl phenolethoxylates and dodecyl phenol ethoxylates (prepared from the phenolsand ethylene oxide, propylene oxide, butylene oxide or mixturesthereof); block polymers prepared from ethylene oxide or propylene oxideand reverse block polymers where the terminal blocks are prepared frompropylene oxide; ethoxylated fatty acids; ethoxylated fatty esters andoils; ethoxylated methyl esters; ethoxylated tristyrylphenol (includingthose prepared from ethylene oxide, propylene oxide, butylene oxide ormixtures thereof); fatty acid esters, glycerol esters, lanolin-basedderivatives, polyethoxylate esters such as polyethoxylated sorbitanfatty acid esters, polyethoxylated sorbitol fatty acid esters andpolyethoxylated glycerol fatty acid esters; other sorbitan derivativessuch as sorbitan esters; polymeric surfactants such as randomcopolymers, block copolymers, alkyd peg (polyethylene glycol) resins,graft or comb polymers and star polymers; polyethylene glycols (pegs);polyethylene glycol fatty acid esters; silicone-based surfactants; andsugar-derivatives such as sucrose esters, alkyl polyglycosides and alkylpolysaccharides.

Useful anionic surfactants include, but are not limited to: alkylarylsulfonic acids and their salts; carboxylated alcohol or alkylphenolethoxylates; diphenyl sulfonate derivatives; lignin and ligninderivatives such as lignosulfonates; maleic or succinic acids or theiranhydrides; olefin sulfonates; phosphate esters such as phosphate estersof alcohol alkoxylates, phosphate esters of alkylphenol alkoxylates andphosphate esters of styryl phenol ethoxylates; protein-basedsurfactants; sarcosine derivatives; styryl phenol ether sulfate;sulfates and sulfonates of oils and fatty acids; sulfates and sulfonatesof ethoxylated alkylphenols; sulfates of alcohols; sulfates ofethoxylated alcohols; sulfonates of amines and amides such asN,N-alkyltaurates; sulfonates of benzene, cumene, toluene, xylene, anddodecyl and tridecylbenzenes; sulfonates of condensed naphthalenes;sulfonates of naphthalene and alkyl naphthalene; sulfonates offractionated petroleum; sulfosuccinamates; and sulfosuccinates and theirderivatives such as dialkyl sulfosuccinate salts.

Useful cationic surfactants include, but are not limited to: amides andethoxylated amides; amines such as N-alkyl propanediamines,tripropylenetriamines and dipropylenetetramines, and ethoxylated amines,ethoxylated diamines and propoxylated amines (prepared from the aminesand ethylene oxide, propylene oxide, butylene oxide or mixturesthereof); amine salts such as amine acetates and diamine salts;quaternary ammonium salts such as quaternary salts, ethoxylatedquaternary salts and diquaternary salts; and amine oxides such asalkyldimethylamine oxides and bis-(2-hydroxyethyl)-alkylamine oxides.

Also useful for the present compositions are mixtures of nonionic andanionic surfactants or mixtures of nonionic and cationic surfactants.Nonionic, anionic and cationic surfactants and their recommended usesare disclosed in a variety of published references includingMcCutcheon's Emulsifiers and Detergents, annual American andInternational Editions published by McCutcheon's Division, TheManufacturing Confectioner Publishing Co.; Sisely and Wood, Encyclopediaof Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964; andA. S. Davidson and B. Milwidsky, Synthetic Detergents, Seventh Edition,John Wiley and Sons, New York, 1987.

Compositions of this invention can also contain formulation auxiliariesand additives, known to those skilled in the art as formulation aids(some of which can be considered to also function as solid diluents,liquid diluents or surfactants). Such formulation auxiliaries andadditives can control: pH (buffers), foaming during processing(antifoams such polyorganosiloxanes), sedimentation of activeingredients (suspending agents), viscosity (thixotropic thickeners),in-container microbial growth (antimicrobials), product freezing(antifreezes), color (dyes/pigment dispersions), wash-off (film formersor stickers), evaporation (evaporation retardants), and otherformulation attributes. Film formers include, for example, polyvinylacetates, polyvinyl acetate copolymers, polyvinylpyrrolidone-vinylacetate copolymer, polyvinyl alcohols, polyvinyl alcohol copolymers andwaxes. Examples of formulation auxiliaries and additives include thoselisted in McCutcheon's Volume 2: Functional Materials, annualInternational and North American editions published by McCutcheon'sDivision, The Manufacturing Confectioner Publishing Co.; and PCTPublication WO 03/024222.

The compound of Formula 1 and any other active ingredients are typicallyincorporated into the present compositions by dissolving the activeingredient in a solvent or by grinding in a liquid or dry diluent.Solutions, including emulsifiable concentrates, can be prepared bysimply mixing the ingredients. If the solvent of a liquid compositionintended for use as an emulsifiable concentrate is water-immiscible, anemulsifier is typically added to emulsify the active-containing solventupon dilution with water. Active ingredient slurries, with particlediameters of up to 2,000 μm can be wet milled using media mills toobtain particles with average diameters below 3 μm. Aqueous slurries canbe made into finished suspension concentrates (see, for example, U.S.Pat. No. 3,060,084) or further processed by spray drying to formwater-dispersible granules. Dry formulations usually require dry millingprocesses, which produce average particle diameters in the 2 to 10 μmrange. Dusts and powders can be prepared by blending and usuallygrinding (such as with a hammer mill or fluid-energy mill). Granules andpellets can be prepared by spraying the active material upon preformedgranular carriers or by agglomeration techniques. See Browning,“Agglomeration”, Chemical Engineering, Dec. 4, 1967, pp 147-48, Perry'sChemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963,pages 8-57 and following, and WO 91/13546. Pellets can be prepared asdescribed in U.S. Pat. No. 4,172,714. Water-dispersible andwater-soluble granules can be prepared as taught in U.S. Pat. No.4,144,050, U.S. Pat. No. 3,920,442 and DE 3,246,493. Tablets can beprepared as taught in U.S. Pat. No. 5,180,587, U.S. Pat. No. 5,232,701and U.S. Pat. No. 5,208,030. Films can be prepared as taught in GB2,095,558 and U.S. Pat. No. 3,299,566.

For further information regarding the art of formulation, see T. S.Woods, “The Formulator's Toolbox—Product Forms for Modern Agriculture”in Pesticide Chemistry and Bioscience, The Food-Environment Challenge,T. Brooks and T. R. Roberts, Eds., Proceedings of the 9th InternationalCongress on Pesticide Chemistry, The Royal Society of Chemistry,Cambridge, 1999, pp. 120-133. See also U.S. Pat. No. 3,235,361, Col. 6,line 16 through Col. 7, line 19 and Examples 10-41; U.S. Pat. No.3,309,192, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12,15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182;U.S. Pat. No. 2,891,855, Col. 3, line 66 through Col. 5, line 17 andExamples 1-4; Klingman, Weed Control as a Science, John Wiley and Sons,Inc., New York, 1961, pp 81-96; Hance et al., Weed Control Handbook, 8thEd., Blackwell Scientific Publications, Oxford, 1989; and Developmentsin formulation technology, PJB Publications, Richmond, UK, 2000.

In the following Examples, all formulations are prepared in conventionalways. Compound numbers refer to compounds in Index Tables A-E. Withoutfurther elaboration, it is believed that one skilled in the art usingthe preceding description can utilize the present invention to itsfullest extent. The following Examples are, therefore, to be construedas merely illustrative, and not limiting of the disclosure in any waywhatsoever. Percentages are by weight except where otherwise indicated.

Example A

High Strength Concentrate compound 30 98.5% silica aerogel 0.5%synthetic amorphous fine silica 1.0%

Example B

Wettable Powder compound 50 65.0% dodecylphenol polyethylene glycolether 2.0% sodium ligninsulfonate 4.0% sodium silicoaluminate 6.0%montmorillonite (calcined) 23.0%

Example C

Granule compound 113 10.0% attapulgite granules (low volatile matter,90.0% 0.71/0.30 mm; U.S.S. No. 25-50 sieves)

Example D

Extruded Pellet compound 191 25.0% anhydrous sodium sulfate 10.0% crudecalcium ligninsulfonate 5.0% sodium alkylnaphthalenesulfonate 1.0%calcium/magnesium bentonite 59.0%

Example E

Emulsifiable Concentrate compound 231 10.0% polyoxyethylene sorbitolhexoleate 20.0% C₆-C₁₀ fatty acid methyl ester 70.0%

Example F

Microemulsion compound 254 5.0% polyvinylpyrrolidone-vinyl acetatecopolymer 30.0% alkylpolyglycoside 30.0% glyceryl monooleate 15.0% water20.0%

Example G

Seed Treatment compound 289 20.00% polyvinylpyrrolidone-vinyl acetatecopolymer 5.00% montan acid wax 5.00% calcium ligninsulfonate 1.00%polyoxyethylene/polyoxypropylene block copolymers 1.00% stearyl alcohol(POE 20) 2.00% polyorganosilane 0.20% colorant red dye 0.05% water65.75%

Example H

Fertilizer Stick compound 352 2.50% pyrrolidone-styrene copolymer 4.80%tristyrylphenyl 16-ethoxylate 2.30% talc 0.80% corn starch 5.00%slow-release fertilizer 36.00% kaolin 38.00% water 10.60%

Example I

Suspension Concentrate compound 30  35% butylpolyoxyethylene/polypropylene block copolymer 4.0% stearicacid/polyethylene glycol copolymer 1.0% styrene acrylic polymer 1.0%xanthan gum 0.1% propylene glycol 5.0% silicone based defoamer 0.1%1,2-benzisothiazolin-3-one 0.1% water 53.7% 

Example J

Emulsion in Water compound 50 10.0% butyl polyoxyethylene/polypropyleneblock copolymer 4.0% stearic acid/polyethylene glycol copolymer 1.0%styrene acrylic polymer 1.0% xanthan gum 0.1% propylene glycol 5.0%silicone based defoamer 0.1% 1,2-benzisothiazolin-3-one 0.1% aromaticpetroleum based hydrocarbon 20.0 water 58.7%

Example K

Oil Dispersion compound 30 25% polyoxyethylene sorbitol hexaoleate 15%organically modified bentonite clay 2.5%  fatty acid methyl ester 57.5% 

Example L

Suspoemulsion compound 50 10.0% imidacloprid 5.0% butylpolyoxyethylene/polypropylene block copolymer 4.0% stearicacid/polyethylene glycol copolymer 1.0% styrene acrylic polymer 1.0%xanthan gum 0.1% propylene glycol 5.0% silicone based defoamer 0.1%1,2-benzisothiazolin-3-one 0.1% aromatic petroleum based hydrocarbon20.0% water 53.7%

Compounds of this invention exhibit activity against a wide spectrum ofinvertebrate pests. These pests include invertebrates inhabiting avariety of environments such as, for example, plant foliage, roots,soil, harvested crops or other foodstuffs, building structures or animalinteguments. These pests include, for example, invertebrates feeding onfoliage (including leaves, stems, flowers and fruits), seeds, wood,textile fibers or animal blood or tissues, and thereby causing injury ordamage to, for example, growing or stored agronomic crops, forests,greenhouse crops, ornamentals, nursery crops, stored foodstuffs or fiberproducts, or houses or other structures or their contents, or beingharmful to animal health or public health. Those skilled in the art willappreciate that not all compounds are equally effective against allgrowth stages of all pests.

These present compounds and compositions are thus useful agronomicallyfor protecting field crops from phytophagous invertebrate pests, andalso nonagronomically for protecting other horticultural crops andplants from phytophagous invertebrate pests. This utility includesprotecting crops and other plants (i.e. both agronomic and nonagronomic)that contain genetic material introduced by genetic engineering (i.e.transgenic) or modified by mutagenesis to provide advantageous traits.Examples of such traits include tolerance to herbicides, resistance tophytophagous pests (e.g., insects, mites, aphids, spiders, nematodes,snails, plant-pathogenic fungi, bacteria and viruses), improved plantgrowth, increased tolerance of adverse growing conditions such as highor low temperatures, low or high soil moisture, and high salinity,increased flowering or fruiting, greater harvest yields, more rapidmaturation, higher quality and/or nutritional value of the harvestedproduct, or improved storage or process properties of the harvestedproducts. Transgenic plants can be modified to express multiple traits.Examples of plants containing traits provided by genetic engineering ormutagenesis include varieties of corn, cotton, soybean and potatoexpressing an insecticidal Bacillus thuringiensis toxin such as YIELDGARD®, KNOCKOUT®, STARLINK®, BOLLGARD®, NuCOTN® and NEWLEAF®, andherbicide-tolerant varieties of corn, cotton, soybean and rapeseed suchas ROUNDUP READY®, LIBERTY LINK®, IMI®, STS® and CLEARFIELD®, as well ascrops expressing N-acetyltransferase (GAT) to provide resistance toglyphosate herbicide, or crops containing the HRA gene providingresistance to herbicides inhibiting acetolactate synthase (ALS). Thepresent compounds and compositions may interact synergistically withtraits introduced by genetic engineering or modified by mutagenesis,thus enhancing phenotypic expression or effectiveness of the traits orincreasing the invertebrate pest control effectiveness of the presentcompounds and compositions. In particular, the present compounds andcompositions may interact synergistically with the phenotypic expressionof proteins or other natural products toxic to invertebrate pests toprovide greater-than-additive control of these pests.

Compositions of this invention can also optionally comprise plantnutrients, e.g., a fertilizer composition comprising at least one plantnutrient selected from nitrogen, phosphorus, potassium, sulfur, calcium,magnesium, iron, copper, boron, manganese, zinc, and molybdenum. Of noteare compositions comprising at least one fertilizer compositioncomprising at least one plant nutrient selected from nitrogen,phosphorus, potassium, sulfur, calcium and magnesium. Compositions ofthe present invention which further comprise at least one plant nutrientcan be in the form of liquids or solids. Of note are solid formulationsin the form of granules, small sticks or tablets. Solid formulationscomprising a fertilizer composition can be prepared by mixing thecompound or composition of the present invention with the fertilizercomposition together with formulating ingredients and then preparing theformulation by methods such as granulation or extrusion. Alternativelysolid formulations can be prepared by spraying a solution or suspensionof a compound or composition of the present invention in a volatilesolvent onto a previous prepared fertilizer composition in the form ofdimensionally stable mixtures, e.g., granules, small sticks or tablets,and then evaporating the solvent.

Examples of agronomic or nonagronomic invertebrate pests include eggs,larvae and adults of the order Lepidoptera, such as armyworms, cutworms,loopers, and heliothines in the family Noctuidae (e.g., pink stem borer(Sesamia inferens Walker), corn stalk borer (Sesamia nonagrioidesLefebvre), southern armyworm (Spodoptera eridania Cramer), fall armyworm(Spodoptera fugiperda J. E. Smith), beet armyworm (Spodoptera exiguaHübner), cotton leafworm (Spodoptera littoralis Boisduval),yellowstriped armyworm (Spodoptera ornithogalli Guenée), black cutworm(Agrotis ipsilon Hufnagel), velvetbean caterpillar (Anticarsiagemmatalis Hübner), green fruitworm (Lithophane antennata Walker),cabbage armyworm (Barathra brassicae Linnaeus), soybean looper(Pseudoplusia includens Walker), cabbage looper (Trichoplusia niHübner), tobacco budworm (Heliothis virescens Fabricius)); borers,casebearers, webworms, coneworms, cabbageworms and skeletonizers fromthe family Pyralidae (e.g., European corn borer (Ostrinia nubilalisHübner), navel orangeworm (Amyelois transitella Walker), corn rootwebworm (Crambus caliginosellus Clemens), sod webworms (Pyralidae:Crambinae) such as sod worm (Herpetogramma licarsisalis Walker),sugarcane stem borer (Chilo infuscatellus Snellen), tomato small borer(Neoleucinodes elegantalis Guenée), green leafroller (Cnaphalocerusmedinalis), grape leaffolder (Desmia funeralis Hübner), melon worm(Diaphania nitidalis Stoll), cabbage center grub (Helluala hydralisGuenée), yellow stem borer (Scirpophaga incertulas Walker), early shootborer (Scirpophaga infuscatellus Snellen), white stem borer (Scirpophagainnotata Walker), top shoot borer (Scirpophaga nivella Fabricius),dark-headed rice borer (Chilo polychrysus Meyrick), cabbage clustercaterpillar (Crocidolomia binotalis English)); leafrollers, budworms,seed worms, and fruit worms in the family Tortricidae (e.g., codlingmoth (Cydia pomonella Linnaeus), grape berry moth (Endopiza viteanaClemens), oriental fruit moth (Grapholita molesta Busck), citrus falsecodling moth (Cryptophlebia leucotreta Meyrick), citrus borer(Ecdytolopha aurantiana Lima), redbanded leafroller (Argyrotaeniavelutinana Walker), obliquebanded leafroller (Choristoneura rosaceanaHarris), light brown apple moth (Epiphyas postvittana Walker), Europeangrape berry moth (Eupoecilia ambiguella Hübner), apple bud moth(Pandemis pyrusana Kearfott), omnivorous leafroller (Platynota stultanaWalsingham), barred fruit-tree tortrix (Pandemis cerasana Hübner), applebrown tortrix (Pandemis heparana Denis & Schiffermüller)); and manyother economically important lepidoptera (e.g., diamondback moth(Plutella xylostella Linnaeus), pink bollworm (Pectinophora gossypiellaSaunders), gypsy moth (Lymantria dispar Linnaeus), peach fruit borer(Carposina niponensis Walsingham), peach twig borer (Anarsia lineatellaZeller), potato tuberworm (Phthorimaea operculella Zeller), spottedteniform leafminer (Lithocolletis blancardella Fabricius), Asiatic appleleafminer (Lithocolletis ringoniella Matsumura), rice leaffolder(Lerodea eufala Edwards), apple leafminer (Leucoptera scitella Zeller));eggs, nymphs and adults of the order Blattodea including cockroachesfrom the families Blattellidae and Blattidae (e.g., oriental cockroach(Blatta orientalis Linnaeus), Asian cockroach (Blatella asahinaiMizukubo), German cockroach (Blattella germanica Linnaeus), brownbandedcockroach (Supella longipalpa Fabricius), American cockroach(Periplaneta americana Linnaeus), brown cockroach (Periplaneta brunneaBurmeister), Madeira cockroach (Leucophaea maderae Fabricius)), smokybrown cockroach (Periplaneta fuliginosa Service), Australian Cockroach(Periplaneta australasiae Fabr.), lobster cockroach (Nauphoeta cinereaOlivier) and smooth cockroach (Symploce pallens Stephens)); eggs, foliarfeeding, fruit feeding, root feeding, seed feeding and vesicular tissuefeeding larvae and adults of the order Coleoptera including weevils fromthe families Anthribidae, Bruchidae, and Curculionidae (e.g., bollweevil (Anthonomus grandis Boheman), rice water weevil (Lissorhoptrusoryzophilus Kuschel), granary weevil (Sitophilus granarius Linnaeus),rice weevil (Sitophilus oryzae Linnaeus)), annual bluegrass weevil(Listronotus maculicollis Dietz), bluegrass billbug (Sphenophorusparvulus Gyllenhal), hunting billbug (Sphenophorus venatus vestitus),Denver billbug (Sphenophorus cicatristriatus Fahraeus)); flea beetles,cucumber beetles, rootworms, leaf beetles, potato beetles, andleafminers in the family Chrysomelidae (e.g., Colorado potato beetle(Leptinotarsa decemlineata Say), western corn rootworm (Diabroticavirgifera virgifera LeConte)); chafers and other beetles from the familyScarabaeidae (e.g., Japanese beetle (Popillia japonica Newman), orientalbeetle (Anomala orientalis Waterhouse, Exomala orientalis (Waterhouse)Baraud), northern masked chafer (Cyclocephala borealis Arrow), southernmasked chafer (Cyclocephala immaculata Olivier or C. lurida Bland), dungbeetle and white grub (Aphodius spp.), black turfgrass ataenius(Ataenius spretulus Haldeman), green June beetle (Cotinis nitidaLinnaeus), Asiatic garden beetle (Maladera castanea Arrow), May/Junebeetles (Phyllophaga spp.) and European chafer (Rhizotrogus majalisRazoumowsky)); carpet beetles from the family Dermestidae; wirewormsfrom the family Elateridae; bark beetles from the family Scolytidae andflour beetles from the family Tenebrionidae.

In addition, agronomic and nonagronomic pests include: eggs, adults andlarvae of the order Dermaptera including earwigs from the familyForficulidae (e.g., European earwig (Forficula auricularia Linnaeus),black earwig (Chelisoches morio Fabricius)); eggs, immatures, adults andnymphs of the orders Hemiptera and Homoptera such as, plant bugs fromthe family Miridae, cicadas from the family Cicadidae, leafhoppers (e.g.Empoasca spp.) from the family Cicadellidae, bed bugs (e.g., Cimexlectularius Linnaeus) from the family Cimicidae, planthoppers from thefamilies Fulgoroidae and Delphacidae, treehoppers from the familyMembracidae, psyllids from the family Psyllidae, whiteflies from thefamily Aleyrodidae, aphids from the family Aphididae, phylloxera fromthe family Phylloxeridae, mealybugs from the family Pseudococcidae,scales from the families Coccidae, Diaspididae and Margarodidae, lacebugs from the family Tingidae, stink bugs from the family Pentatomidae,chinch bugs (e.g., hairy chinch bug (Blissus leucopterus hirtusMontandon) and southern chinch bug (Blissus insularis Barber)) and otherseed bugs from the family Lygaeidae, spittlebugs from the familyCercopidae squash bugs from the family Coreidae, and red bugs and cottonstainers from the family Pyrrhocoridae.

Agronomic and nonagronomic pests also include: eggs, larvae, nymphs andadults of the order Acari (mites) such as spider mites and red mites inthe family Tetranychidae (e.g., European red mite (Panonychus ulmiKoch), two spotted spider mite (Tetranychus urticae Koch), McDaniel mite(Tetranychus mcdanieli McGregor)); flat mites in the familyTenuipalpidae (e.g., citrus flat mite (Brevipalpus lewisi McGregor));rust and bud mites in the family Eriophyidae and other foliar feedingmites and mites important in human and animal health, i.e. dust mites inthe family Epidermoptidae, follicle mites in the family Demodicidae,grain mites in the family Glycyphagidae; ticks in the family Ixodidae,commonly known as hard ticks (e.g., deer tick (Ixodes scapularis Say),Australian paralysis tick (Ixodes holocyclus Neumann), American dog tick(Dermacentor variabilis Say), lone star tick (Amblyomma americanumLinnaeus)) and ticks in the family Argasidae, commonly known as softticks (e.g., relapsing fever tick (Ornithodoros turicata), common fowltick (Argas radiatus)); scab and itch mites in the families Psoroptidae,Pyemotidae, and Sarcoptidae; eggs, adults and immatures of the orderOrthoptera including grasshoppers, locusts and crickets (e.g., migratorygrasshoppers (e.g., Melanoplus sanguinipes Fabricius, M. differentialisThomas), American grasshoppers (e.g., Schistocerca americana Drury),desert locust (Schistocerca gregaria Forskal), migratory locust (Locustamigratoria Linnaeus), bush locust (Zonocerus spp.), house cricket(Acheta domesticus Linnaeus), mole crickets (e.g., tawny mole cricket(Scapteriscus vicinus Scudder) and southern mole cricket (Scapteriscusborellii Giglio-Tos)); eggs, adults and immatures of the order Dipteraincluding leafminers (e.g., Liriomyza spp. such as serpentine vegetableleafminer (Liriomyza sativae Blanchard)), midges, fruit flies(Tephritidae), frit flies (e.g., Oscinella frit Linnaeus), soil maggots,house flies (e.g., Musca domestica Linnaeus), lesser house flies (e.g.,Fannia canicularis Linnaeus, F. femoralis Stein), stable flies (e.g.,Stomoxys calcitrans Linnaeus), face flies, horn flies, blow flies (e.g.,Chrysomya spp., Phormia spp.), and other muscoid fly pests, horse flies(e.g., Tabanus spp.), bot flies (e.g., Gastrophilus spp., Oestrus spp.),cattle grubs (e.g., Hypoderma spp.), deer flies (e.g., Chrysops spp.),keds (e.g., Melophagus ovinus Linnaeus) and other Brachycera, mosquitoes(e.g., Aedes spp., Anopheles spp., Culex spp.), black flies (e.g.,Prosimulium spp., Simulium spp.), biting midges, sand flies, sciarids,and other Nematocera; eggs, adults and immatures of the orderThysanoptera including onion thrips (Thrips tabaci Lindeman), flowerthrips (Frankliniella spp.), and other foliar feeding thrips; insectpests of the order Hymenoptera including ants of the Family Formicidaeincluding the Florida carpenter ant (Camponotus floridanus Buckley), redcarpenter ant (Camponotus ferrugineus Fabricius), black carpenter ant(Camponotus pennsylvanicus De Geer), white-footed ant (Technomyrmexalbipes fr. Smith), big headed ants (Pheidole sp.), ghost ant (Tapinomamelanocephalum Fabricius); Pharaoh ant (Monomorium pharaonis Linnaeus),little fire ant (Wasmannia auropunctata Roger), fire ant (Solenopsisgeminata Fabricius), red imported fire ant (Solenopsis invicta Buren),Argentine ant (Iridomyrmex humilis Mayr), crazy ant (Paratrechinalongicornis Latreille), pavement ant (Tetramorium caespitum Linnaeus),cornfield ant (Lasius alienus Förster) and odorous house ant (Tapinomasessile Say). Other Hymenoptera including bees (including carpenterbees), hornets, yellow jackets, wasps, and sawflies (Neodiprion spp.;Cephus spp.); insect pests of the order Isoptera including termites inthe Termitidae (e.g., Macrotermes sp., Odontotermes obesus Rambur),Kalotermitidae (e.g., Cryptotermes sp.), and Rhinotermitidae (e.g.,Reticulitermes sp., Coptotermes sp., Heterotermes tenuis Hagen)families, the eastern subterranean termite (Reticulitermes flavipesKollar), western subterranean termite (Reticulitermes hesperus Banks),Formosan subterranean termite (Coptotermes formosanus Shiraki), WestIndian drywood termite (Incisitermes immigrans Snyder), powder posttermite (Cryptotermes brevis Walker), drywood termite (Incisitermessnyderi Light), southeastern subterranean termite (Reticulitermesvirginicus Banks), western drywood termite (Incisitermes minor Hagen),arboreal termites such as Nasutitermes sp. and other termites ofeconomic importance; insect pests of the order Thysanura such assilverfish (Lepisma saccharina Linnaeus) and firebrat (Thermobiadomestica Packard); insect pests of the order Mallophaga and includingthe head louse (Pediculus humanus capitis De Geer), body louse(Pediculus humanus Linnaeus), chicken body louse (Menacanthus stramineusNitszch), dog biting louse (Trichodectes canis De Geer), fluff louse(Goniocotes gallinae De Geer), sheep body louse (Bovicola ovis Schrank),short-nosed cattle louse (Haematopinus eurysternus Nitzsch), long-nosedcattle louse (Linognathus vituli Linnaeus) and other sucking and chewingparasitic lice that attack man and animals; insect pests of the orderSiphonoptera including the oriental rat flea (Xenopsylla cheopisRothschild), cat flea (Ctenocephalides felis Bouche), dog flea(Ctenocephalides canis Curtis), hen flea (Ceratophyllus gallinaeSchrank), sticktight flea (Echidnophaga gallinacea Westwood), human flea(Pulex irritans Linnaeus) and other fleas afflicting mammals and birds.Additional arthropod pests covered include: spiders in the order Araneaesuch as the brown recluse spider (Loxosceles reclusa Gertsch & Mulaik)and the black widow spider (Latrodectus mactans Fabricius), andcentipedes in the order Scutigeromorpha such as the house centipede(Scutigera coleoptrata Linnaeus).

Examples of invertebrate pests of stored grain include larger grainborer (Prostephanus truncatus), lesser grain borer (Rhyzoperthadominica), rice weevil (Stiophilus oryzae), maize weevil (Stiophiluszeamais), cowpea weevil (Callosobruchus maculatus), red flour beetle(Tribolium castaneum), granary weevil (Stiophilus granarius), Indianmeal moth (Plodia interpunctella), Mediterranean flour beetle (Ephestiakuhniella) and flat or rusty grain beetle (Cryptolestis ferrugineus).

Compounds of the invention show particularly high activity against pestsin the order Lepidoptera (e.g., Alabama argillacea Hübner (cotton leafworm), Archips argyrospila Walker (fruit tree leaf roller), A. rosanaLinnaeus (European leaf roller) and other Archips species, Chilosuppressalis Walker (rice stem borer), Cnaphalocrosis medinalis Guenée(rice leaf roller), Crambus caliginosellus Clemens (corn root webworm),Crambus teterrellus Zincken (bluegrass webworm), Cydia pomonellaLinnaeus (codling moth), Earias insulana Boisduval (spiny bollworm),Earias vittella Fabricius (spotted bollworm), Helicoverpa armigeraHübner (American bollworm), Helicoverpa zea Boddie (corn earworm),Heliothis virescens Fabricius (tobacco budworm), Herpetogrammalicarsisalis Walker (sod webworm), Lobesia botrana Denis &Schiffermfiller (grape berry moth), Pectinophora gossypiella Saunders(pink bollworm), Phyllocnistis citrella Stainton (citrus leafminer),Pieris brassicae Linnaeus (large white butterfly), Pieris rapae Linnaeus(small white butterfly), Plutella xylostella Linnaeus (diamondbackmoth), Spodoptera exigua Hübner (beet armyworm), Spodoptera lituraFabricius (tobacco cutworm, cluster caterpillar), Spodoptera frugiperdaJ. E. Smith (fall armyworm), Trichoplusia ni Hübner (cabbage looper) andTuta absoluta Meyrick (tomato leafminer)).

Compounds of the invention also have significant activity on membersfrom the order Homoptera including: Acyrthosiphon pisum Harris (peaaphid), Aphis craccivora Koch (cowpea aphid), Aphis fabae Scopoli (blackbean aphid), Aphis gossypii Glover (cotton aphid, melon aphid), Aphispomi De Geer (apple aphid), Aphis spiraecola Patch (spirea aphid),Aulacorthum solani Kaltenbach (foxglove aphid), Chaetosiphon fragaefoliiCockerell (strawberry aphid), Diuraphis noxia Kurdjumov/Mordvilko(Russian wheat aphid), Dysaphis plantaginea Paaserini (rosy appleaphid), Eriosoma lanigerum Hausmann (woolly apple aphid), Hyalopteruspruni Geoffroy (mealy plum aphid), Lipaphis erysimi Kaltenbach (turnipaphid), Metopolophium dirrhodum Walker (cereal aphid), Macrosiphumeuphorbiae Thomas (potato aphid), Myzus persicae Sulzer (peach-potatoaphid, green peach aphid), Nasonovia ribisnigri Mosley (lettuce aphid),Pemphigus spp. (root aphids and gall aphids), Rhopalosiphum maidis Fitch(corn leaf aphid), Rhopalosiphum padi Linnaeus (bird cherry-oat aphid),Schizaphis graminum Rondani (greenbug), Sitobion avenae Fabricius(English grain aphid), Therioaphis maculata Buckton (spotted alfalfaaphid), Toxoptera aurantii Boyer de Fonscolombe (black citrus aphid),and Toxoptera citricida Kirkaldy (brown citrus aphid); Adelges spp.(adelgids); Phylloxera devastatrix Pergande (pecan phylloxera); Bemisiatabaci Gennadius (tobacco whitefly, sweetpotato whitefly), Bemisiaargentifolii Bellows & Perring (silverleaf whitefly), Dialeurodes citriAshmead (citrus whitefly) and Trialeurodes vaporariorum Westwood(greenhouse whitefly); Empoasca fabae Harris (potato leafhopper),Laodelphax striatellus Fallen (smaller brown planthopper), Macrolestesquadrilineatus Forbes (aster leafhopper), Nephotettix cinticeps Uhler(green leafhopper), Nephotettix nigropictus Stål (rice leafhopper),Nilaparvata lugens Stål (brown planthopper), Peregrinus maidis Ashmead(corn planthopper), Sogatella furcifera Horvath (white-backedplanthopper), Sogatodes orizicola Muir (rice delphacid), Typhlocybapomaria McAtee white apple leafhopper, Erythroneoura spp. (grapeleafhoppers); Magicidada septendecim Linnaeus (periodical cicada);Icerya purchasi Maskell (cottony cushion scale), Quadraspidiotusperniciosus Comstock (San Jose scale); Planococcus citri Risso (citrusmealybug); Pseudococcus spp. (other mealybug complex); Cacopsyllapyricola Foerster (pear psylla), Trioza diospyri Ashmead (persimmonpsylla).

Compounds of this invention may also have activity on members from theorder Hemiptera including: Acrosternum hilare Say (green stink bug),Anasa tristis De Geer (squash bug), Blissus leucopterus leucopterus Say(chinch bug), Cimex lectularius Linnaeus (bed bug) Corythuca gossypiiFabricius (cotton lace bug), Cyrtopeltis modesta Distant (tomato bug),Dysdercus suturellus Herrich-Schäffer (cotton stainer), Euchistus servusSay (brown stink bug), Euchistus variolarius Palisot de Beauvois(one-spotted stink bug), Graptosthetus spp. (complex of seed bugs),Leptoglossus corculus Say (leaf-footed pine seed bug), Lygus lineolarisPalisot de Beauvois (tarnished plant bug), Nezara viridula Linnaeus(southern green stink bug), Oebalus pugnax Fabricius (rice stink bug),Oncopeltus fasciatus Dallas (large milkweed bug), Pseudatomoscelisseriatus Reuter (cotton fleahopper). Other insect orders controlled bycompounds of the invention include Thysanoptera (e.g., Frankliniellaoccidentalis Pergande (western flower thrips), Scirthothrips citriMoulton (citrus thrips), Sericothrips variabilis Beach (soybean thrips),and Thrips tabaci Lindeman (onion thrips); and the order Coleoptera(e.g., Leptinotarsa decemlineata Say (Colorado potato beetle), Epilachnavarivestis Mulsant (Mexican bean beetle) and wireworms of the generaAgriotes, Athous or Limonius).

Compounds of the present invention also have activity on members of theClasses Nematoda, Cestoda, Trematoda, and Acanthocephala includingeconomically important members of the orders Strongylida, Ascaridida,Oxyurida, Rhabditida, Spirurida, and Enoplida such as but not limited toeconomically important agricultural pests (i.e. root knot nematodes inthe genus Meloidogyne, lesion nematodes in the genus Pratylenchus,stubby root nematodes in the genus Trichodorus, etc.) and animal andhuman health pests (i.e. all economically important flukes, tapeworms,and roundworms, such as Strongylus vulgaris in horses, Toxocara canis indogs, Haemonchus contortus in sheep, Dirofilaria immitis Leidy in dogs,Anoplocephala perfoliata in horses, Fasciola hepatica Linnaeus inruminants, etc.).

Note that some contemporary classification systems place Homoptera as asuborder within the order Hemiptera.

Of note is use of compounds of this invention for controlling potatoleafhopper (Empoasca fabae). Of note is use of compounds of thisinvention for controlling corn planthopper (Peregrinus maidis). Of noteis use of compounds of this invention for controlling cotton melon aphid(Aphis gossypii). Of note is use of compounds of this invention forcontrolling green peach aphid (Myzus persicae). Of note is use ofcompounds of this invention for controlling diamondback moth (Plutellaxylostella). Of note is use of compounds of this invention forcontrolling fall armyworm (Spodoptera frugiperda).

Of note is use of compounds of this invention for controlling southerngreen stink bug (Nezara viridula), western tarnished plant bug (Lygushesperus), rice water weevil (Lissorhoptrus oryzophilus), rice brownplanthopper (Nilaparvata lugens), rice green leafhopper (Nephotettixvirescens) and striped rice borer (Chilo suppressalis).

Compounds of this invention can also be mixed with one or more otherbiologically active compounds or agents including insecticides,fungicides, nematocides, bactericides, acaricides, herbicides, herbicidesafeners, growth regulators such as insect molting inhibitors androoting stimulants, chemosterilants, semiochemicals, repellents,attractants, pheromones, feeding stimulants, other biologically activecompounds or entomopathogenic bacteria, virus or fungi to form amulti-component pesticide giving an even broader spectrum of agronomicand nonagronomic utility. Thus the present invention also pertains to acomposition comprising a biologically effective amount of a compound ofFormula 1, an N-oxide, or salt thereof, at least one additionalcomponent selected from the group consisting of surfactants, soliddiluents and liquid diluents, and at least one additional biologicallyactive compound or agent. For mixtures of the present invention, theother biologically active compounds or agents can be formulated togetherwith the present compounds, including the compounds of Formula 1, toform a premix, or the other biologically active compounds or agents canbe formulated separately from the present compounds, including thecompounds of Formula 1, and the two formulations combined togetherbefore application (e.g., in a spray tank) or, alternatively, applied insuccession.

Examples of such biologically active compounds or agents with whichcompounds of this invention can be formulated are insecticides such asabamectin, acephate, acequinocyl, acetamiprid, acrinathrin, amidoflumet,amitraz, avermectin, azadirachtin, azinphos-methyl, bensultap,bifenthrin, bifenazate, bistrifluoron, borate, buprofezin, cadusafos,carbaryl, carbofuran, cartap, carzol, chlorantraniliprole, chlorfenapyr,chlorfluazuron, chlorpyrifos, chlorpyrifos-methyl, chromafenozide,clofentezin, clothianidin, cyantraniliprole, cyflumetofen, cyfluthrin,beta-cyfluthrin, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin,cypermethrin, alpha-cypermethrin, zeta-cypermethrin, cyromazine,deltamethrin, diafenthiuron, diazinon, dieldrin, diflubenzuron,dimefluthrin, dimehypo, dimethoate, dinotefuran, diofenolan, emamectin,endosulfan, esfenvalerate, ethiprole, etofenprox, etoxazole, fenbutatinoxide, fenothiocarb, fenoxycarb, fenpropathrin, fenvalerate, fipronil,flonicamid, flubendiamide, flucythrinate, flufenerim, flufenoxuron,fluvalinate, tau-fluvalinate, fonophos, formetanate, fosthiazate,halofenozide, hexaflumuron, hexythiazox, hydramethylnon, imidacloprid,indoxacarb, insecticidal soaps, isofenphos, lufenuron, malathion,meperfluthrin, metaflumizone, metaldehyde, methamidophos, methidathion,methiodicarb, methomyl, methoprene, methoxychlor, metofluthrin,monocrotophos, methoxyfenozide, nitenpyram, nithiazine, novaluron,noviflumuron, oxamyl, parathion, parathion-methyl, permethrin, phorate,phosalone, phosmet, phosphamidon, pirimicarb, profenofos, profluthrin,propargite, protrifenbute, pymetrozine, pyrafluprole, pyrethrin,pyridaben, pyridalyl, pyrifluquinazon, pyriprole, pyriproxyfen,rotenone, ryanodine, spinetoram, spinosad, spirodiclofen, spiromesifen,spirotetramat, sulprofos, sulfoxaflor, tebufenozide, tebufenpyrad,teflubenzuron, tefluthrin, terbufos, tetrachlorvinphos, tetramethrin,tetramethylfluthrin, thiacloprid, thiamethoxam, thiodicarb,thiosultap-sodium, tolfenpyrad, tralomethrin, triazamate, trichlorfon,triflumuron, Bacillus thuringiensis delta-endotoxins, entomopathogenicbacteria, entomopathogenic viruses and entomopathogenic fungi.

Of note are insecticides such as abamectin, acetamiprid, acrinathrin,amitraz, avermectin, azadirachtin, bensultap, bifenthrin, buprofezin,cadusafos, carbaryl, cartap, chlorantraniliprole, chlorfenapyr,chlorpyrifos, clothianidin, cyantraniliprole, cyfluthrin,beta-cyfluthrin, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin,cypermethrin, alpha-cypermethrin, zeta-cypermethrin, cyromazine,deltamethrin, dieldrin, dinotefuran, diofenolan, emamectin, endosulfan,esfenvalerate, ethiprole, etofenprox, etoxazole, fenothiocarb,fenoxycarb, fenvalerate, fipronil, flonicamid, flubendiamide,flufenoxuron, fluvalinate, formetanate, fosthiazate, hexaflumuron,hydramethylnon, imidacloprid, indoxacarb, lufenuron, metaflumizone,methiodicarb, methomyl, methoprene, methoxyfenozide, nitenpyram,nithiazine, novaluron, oxamyl, pymetrozine, pyrethrin, pyridaben,pyridalyl, pyriproxyfen, ryanodine, spinetoram, spinosad, spirodiclofen,spiromesifen, spirotetramat, tebufenozide, tetramethrin, thiacloprid,thiamethoxam, thiodicarb, thiosultap-sodium, tralomethrin, triazamate,triflumuron, Bacillus thuringiensis delta-endotoxins, all strains ofBacillus thuringiensis and all strains of Nucleo polyhydrosis viruses.

One embodiment of biological agents for mixing with compounds of thisinvention include entomopathogenic bacteria such as Bacillusthuringiensis, and the encapsulated delta-endotoxins of Bacillusthuringiensis such as MVP® and MVPII® bioinsecticides prepared by theCellCap® process (CellCap®, MVP® and MVPII® are trademarks of MycogenCorporation, Indianapolis, Ind., USA); entomopathogenic fungi such asgreen muscardine fungus; and entomopathogenic (both naturally occurringand genetically modified) viruses including baculovirus, nucleopolyhedrovirus (NPV) such as Helicoverpa zea nucleopolyhedrovirus (HzNPV),Anagrapha falcifera nucleopolyhedrovirus (AfNPV); and granulosis virus(GV) such as Cydia pomonella granulosis virus (CpGV).

Of particular note is such a combination where the other invertebratepest control active ingredient belongs to a different chemical class orhas a different site of action than the compound of Formula 1. Incertain instances, a combination with at least one other invertebratepest control active ingredient having a similar spectrum of control buta different site of action will be particularly advantageous forresistance management. Thus, a composition of the present invention canfurther comprise a biologically effective amount of at least oneadditional invertebrate pest control active ingredient having a similarspectrum of control but belonging to a different chemical class orhaving a different site of action. These additional biologically activecompounds or agents include, but are not limited to, sodium channelmodulators such as bifenthrin, cypermethrin, cyhalothrin,lambda-cyhalothrin, cyfluthrin, beta-cyfluthrin, deltamethrin,dimefluthrin, esfenvalerate, fenvalerate, indoxacarb, metofluthrin,profluthrin, pyrethrin and tralomethrin; cholinesterase inhibitors suchas chlorpyrifos, methomyl, oxamyl, thiodicarb and triazamate;neonicotinoids such as acetamiprid, clothianidin, dinotefuran,imidacloprid, nitenpyram, nithiazine, thiacloprid and thiamethoxam;insecticidal macrocyclic lactones such as spinetoram, spinosad,abamectin, avermectin and emamectin; GABA (γ-aminobutyric acid)-gatedchloride channel antagonists such as avermectin or blockers such asethiprole and fipronil; chitin synthesis inhibitors such as buprofezin,cyromazine, flufenoxuron, hexaflumuron, lufenuron, novaluron,noviflumuron and triflumuron; juvenile hormone mimics such asdiofenolan, fenoxycarb, methoprene and pyriproxyfen; octopamine receptorligands such as amitraz; molting inhibitors and ecdysone agonists suchas azadirachtin, methoxyfenozide and tebufenozide; ryanodine receptorligands such as ryanodine, anthranilic diamides such aschlorantraniliprole, cyantraniliprole and flubendiamide; nereistoxinanalogs such as cartap; mitochondrial electron transport inhibitors suchas chlorfenapyr, hydramethylnon and pyridaben; lipid biosynthesisinhibitors such as spirodiclofen and spiromesifen; cyclodieneinsecticides such as dieldrin or endosulfan; pyrethroids; carbamates;insecticidal ureas; and biological agents including nucleopolyhedroviruses (NPV), members of Bacillus thuringiensis, encapsulateddelta-endotoxins of Bacillus thuringiensis, and other naturallyoccurring or genetically modified insecticidal viruses.

Further examples of biologically active compounds or agents with whichcompounds of this invention can be formulated are: fungicides such as1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,acibenzolar, aldimorph, amisulbrom, azaconazole, azoxystrobin,benalaxyl, benomyl, benthiavalicarb, benthiavalicarb-isopropyl,binomial, biphenyl, bitertanol, blasticidin-S, Bordeaux mixture(Tribasic copper sulfate), boscalid/nicobifen, bromuconazole,bupirimate, buthiobate, carboxin, carpropamid, captafol, captan,carbendazim, chloroneb, chlorothalonil, chlozolinate, clotrimazole,copper oxychloride, copper salts such as copper sulfate and copperhydroxide, cyazofamid, cyflunamid, cymoxanil, cyproconazole, cyprodinil,dichlofluanid, diclocymet, diclomezine, dicloran, diethofencarb,difenoconazole, dimethomorph, dimoxystrobin, diniconazole,diniconazole-M, dinocap, discostrobin, dithianon, dodemorph, dodine,econazole, etaconazole, edifenphos, epoxiconazole, ethaboxam, ethirimol,ethridiazole, famoxadone, fenamidone, fenarimol, fenbuconazole,fencaramid, fenfuram, fenhexamide, fenoxanil, fenpiclonil, fenpropidin,fenpropimorph, fentin acetate, fentin hydroxide, ferbam, ferfurazoate,ferimzone, fluazinam, fludioxonil, flumetover, fluopicolide,fluoxastrobin, fluquinconazole, fluquinconazole, flusilazole,flusulfamide, flutolanil, flutriafol, fluxapyroxad, folpet,fosetyl-aluminum, fthalide, fuberidazole, furalaxyl, furametpyr,hexaconazole, hymexazole, guazatine, imazalil, imibenconazole,iminoctadine, iodicarb, ipconazole, iprobenfos, iprodione, iprovalicarb,isoconazole, isoprothiolane, isotianil, kasugamycin, kresoxim-methyl,mancozeb, mandipropamid, maneb, mapanipyrin, mefenoxam, mepronil,metalaxyl, metconazole, methasulfocarb, metiram,metominostrobin/fenominostrobin, mepanipyrim, metrafenone, miconazole,myclobutanil, neo-asozin (ferric methanearsonate), nuarimol,octhilinone, ofurace, orysastrobin, oxadixyl, oxolinic acid,oxpoconazole, oxycarboxin, paclobutrazol, penconazole, pencycuron,penflufen, penthiopyrad, perfurazoate, phosphonic acid, phthalide,picobenzamid, picoxystrobin, polyoxin, probenazole, prochloraz,procymidone, propamocarb, propamocarb-hydrochloride, propiconazole,propineb, proquinazid, prothioconazole, pyraclostrobin, pyrametostrobin,pyraoxystrobin, pryazophos, pyrifenox, pyrimethanil, pyrifenox,pyriofenone, pyroInitrine, pyroquilon, quinconazole, quinoxyfen,quintozene, silthiofam, simeconazole, spiroxamine, streptomycin, sulfur,tebuconazole, tebufloquin, techrazene, tecloftalam, tecnazene,tetraconazole, thiabendazole, thifluzamide, thiophanate,thiophanate-methyl, thiram, tiadinil, tolclofos-methyl, tolyfluanid,triadimefon, triadimenol, triarimol, triazoxide, tridemorph,trimorphamide, tricyclazole, trifloxystrobin, triforine, triticonazole,uniconazole, validamycin, valifenalate, vinclozolin, zineb, ziram, andzoxamide; nematocides such as aldicarb, imicyafos, oxamyl andfenamiphos; bactericides such as streptomycin; acaricides such asamitraz, chinomethionat, chlorobenzilate, cyhexatin, dicofol,dienochlor, etoxazole, fenazaquin, fenbutatin oxide, fenpropathrin,fenpyroximate, hexythiazox, propargite, pyridaben and tebufenpyrad.

Of note are fungicides and compositions comprising fungicides such as1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,azoxystrobin, copper hydroxide, cymoxanil, cyproconazole,difenoconazole, famoxadone, fenoxanil, ferimzone, flusilazole,flutolanil, fthalide, furametpyr, hexaconazole, isoprothiolane,isotianil, kasugamycin, mancozeb, metominostrobin, orysastrobin,pencycuron, penthiopyrad, picoxystrobin, probenazole, propiconazole,proquinazid, pyroquilon, simeconazole, tiadinil, tricyclazole,trifloxystrobin and validamycin.

In certain instances, combinations of a compound of this invention withother biologically active (particularly invertebrate pest control)compounds or agents (i.e. active ingredients) can result in agreater-than-additive (i.e. synergistic) effect. Reducing the quantityof active ingredients released in the environment while ensuringeffective pest control is always desirable. When synergism ofinvertebrate pest control active ingredients occurs at application ratesgiving agronomically satisfactory levels of invertebrate pest control,such combinations can be advantageous for reducing crop production costand decreasing environmental load.

Compounds of this invention and compositions thereof can be applied toplants genetically transformed to express proteins toxic to invertebratepests (such as Bacillus thuringiensis delta-endotoxins). Such anapplication may provide a broader spectrum of plant protection and beadvantageous for resistance management. The effect of the exogenouslyapplied invertebrate pest control compounds of this invention may besynergistic with the expressed toxin proteins.

General references for these agricultural protectants (i.e.insecticides, fungicides, nematocides, acaricides, herbicides andbiological agents) include The Pesticide Manual, 13th Edition, C. D. S.Tomlin, Ed., British Crop Protection Council, Farnham, Surrey, U.K.,2003 and The BioPesticide Manual, 2^(nd) Edition, L. G. Copping, Ed.,British Crop Protection Council, Farnham, Surrey, U.K., 2001.

For embodiments where one or more of these various mixing partners areused, the weight ratio of these various mixing partners (in total) tothe compound of Formula 1, an N-oxide, or salt thereof, is typicallybetween about 1:3000 and about 3000:1. Of note are weight ratios betweenabout 1:300 and about 300:1 (for example ratios between about 1:30 andabout 30:1). One skilled in the art can easily determine through simpleexperimentation the biologically effective amounts of active ingredientsnecessary for the desired spectrum of biological activity. It will beevident that including these additional components can expand thespectrum of invertebrate pests controlled beyond the spectrum controlledby the compound of Formula 1 alone.

Table A lists specific combinations of a compound of Formula 1 withother invertebrate pest control agents illustrative of the mixtures,compositions and methods of the present invention. The first column ofTable A lists the specific invertebrate pest control agents (e.g.,“Abamectin” in the first line). The second column of Table A lists themode of action (if known) or chemical class of the invertebrate pestcontrol agents. The third column of Table A lists embodiment(s) ofranges of weight ratios for rates at which a compound of Formula 1 canbe applied relative to an invertebrate pest control agent (e.g., “50:1to 1:50” of a compound of Formula 1 relative to abamectin by weight).Thus, for example, the first line of Table A specifically discloses thecombination of a compound of Formula 1 with abamectin can be applied ina weight ratio between 50:1 to 1:50. The remaining lines of Table A areto be construed similarly. Of further note Table A lists specificcombinations of a compound of Formula 1 with other invertebrate pestcontrol agents illustrative of the mixtures, compositions and methods ofthe present invention and includes additional embodiments of weightratio ranges for application rates.

TABLE A Invertebrate Pest Control Mode of Action or Typical AgentChemical Class Weight Ratio Abamectin macrocyclic lactones 50:1 to 1:50Acetamiprid neonicotinoids 150:1 to 1:200 Amitraz octopamine receptorligands 200:1 to 1:100 Avermectin macrocyclic lactones 50:1 to 1:50Azadirachtin ecdysone agonists 100:1 to 1:120 Beta-cyfluthrin sodiumchannel modulators 150:1 to 1:200 Bifenthrin sodium channel modulators100:1 to 1:10  Buprofezin chitin synthesis inhibitors 500:1 to 1:50 Cartap nereistoxin analogs 100:1 to 1:200 Chloran- ryanodine receptorligands 100:1 to 1:120 traniliprole Chlorfenapyr mitochondrial electron300:1 to 1:200 transport inhibitors Chlorpyrifos cholinesteraseinhibitors 500:1 to 1:200 Clothianidin neonicotinoids 100:1 to 1:400Cyantraniliprole ryanodine receptor ligands 100:1 to 1:120 Cyfluthrinsodium channel modulators 150:1 to 1:200 Cyhalothrin sodium channelmodulators 150:1 to 1:200 Cypermethrin sodium channel modulators 150:1to 1:200 Cyromazine chitin synthesis inhibitors 400:1 to 1:50 Deltamethrin sodium channel modulators  50:1 to 1:400 Dieldrincyclodiene insecticides 200:1 to 1:100 Dinotefuran neonicotinoids 150:1to 1:200 Diofenolan molting inhibitor 150:1 to 1:200 Emamectinmacrocyclic lactones 50:1 to 1:10 Endosulfan cyclodiene insecticides200:1 to 1:100 Esfenvalerate sodium channel modulators 100:1 to 1:400Ethiprole GABA-regulated chloride 200:1 to 1:100 channel blockersFenothiocarb 150:1 to 1:200 Fenoxycarb juvenile hormone mimics 500:1 to1:100 Fenvalerate sodium channel modulators 150:1 to 1:200 FipronilGABA-regulated chloride 150:1 to 1:100 channel blockers Flonicamid 200:1to 1:100 Flubendiamide ryanodine receptor ligands 100:1 to 1:120Flufenoxuron chitin synthesis inhibitors 200:1 to 1:100 Hexaflumuronchitin synthesis inhibitors 300:1 to 1:50  Hydramethylnon mitochondrialelectron 150:1 to 1:250 transport inhibitors Imidacloprid neonicotinoids1000:1 to 1:1000 Indoxacarb sodium channel modulators 200:1 to 1:50 Lambda- sodium channel modulators  50:1 to 1:250 cyhalothrin Lufenuronchitin synthesis inhibitors 500:1 to 1:250 Metaflumizone 200:1 to 1:200Methomyl cholinesterase inhibitors 500:1 to 1:100 Methoprene juvenilehormone mimics 500:1 to 1:100 Methoxyfenozide ecdysone agonists 50:1 to1:50 Nitenpyram neonicotinoids 150:1 to 1:200 Nithiazine neonicotinoids150:1 to 1:200 Novaluron chitin synthesis inhibitors 500:1 to 1:150Oxamyl cholinesterase inhibitors 200:1 to 1:200 Pymetrozine 200:1 to1:100 Pyrethrin sodium channel modulators 100:1 to 1:10  Pyridabenmitochondrial electron 200:1 to 1:100 transport inhibitors Pyridalyl200:1 to 1:100 Pyriproxyfen juvenile hormone mimics 500:1 to 1:100Ryanodine ryanodine receptor ligands 100:1 to 1:120 Spinetorammacrocyclic lactones 150:1 to 1:100 Spinosad macrocyclic lactones 500:1to 1:10  Spirodiclofen lipid biosynthesis 200:1 to 1:200 inhibitorsSpiromesifen lipid biosynthesis 200:1 to 1:200 inhibitors Tebufenozideecdysone agonists 500:1 to 1:250 Thiacloprid neonicotinoids 100:1 to1:200 Thiamethoxam neonicotinoids 1250:1 to 1:1000 Thiodicarbcholinesterase inhibitors 500:1 to 1:400 Thiosultap- 150:1 to 1:100sodium Tralomethrin sodium channel modulators 150:1 to 1:200 Triazamatecholinesterase inhibitors 250:1 to 1:100 Triflumuron chitin synthesisinhibitors 200:1 to 1:100 Bacillus biological agents 50:1 to 1:10thuringiensis Bacillus biological agents 50:1 to 1:10 thuringiensisdelta-endotoxin NPV (e.g., biological agents 50:1 to 1:10 Gemstar)

Of note is the composition of the present invention wherein the at leastone additional biologically active compound or agent is selected fromthe Invertebrate Pest Control Agents listed in Table A above.

The weight ratios of a compound, including a compound of Formula 1, anN-oxide, or salt thereof, to the additional invertebrate pest controlagent typically are between 1000:1 and 1:1000, with one embodiment beingbetween 500:1 and 1:500, another embodiment being between 250:1 and1:200 and another embodiment being between 100:1 and 1:50.

Listed below in Tables B1 to B81 are embodiments of specificcompositions comprising a compound of Formula 1 (compound numbers (Cmpd.No.) refer to compounds in Index Tables A-E) and an additionalinvertebrate pest control agent.

TABLE B1 Mixture Cmpd. Invertebrate Pest No. No. and Control Agent B1-11 and Abamectin B1-2 1 and Acetamiprid B1-3 1 and Amitraz B1-4 1 andAvermectin B1-5 1 and Azadirachtin B1-5a 1 and Bensultap B1-6 1 andBeta-cyfluthrin B1-7 1 and Bifenthrin B1-8 1 and Buprofezin B1-9 1 andCartap B1-10 1 and Chlorantraniliprole B1-11 1 and Chlorfenapyr B1-12 1and Chlorpyrifos B1-13 1 and Clothianidin B1-14 1 and CyantraniliproleB1-15 1 and Cyfluthrin B1-16 1 and Cyhalothrin B1-17 1 and CypermethrinB1-18 1 and Cyromazine B1-19 1 and Deltamethrin B1-20 1 and DieldrinB1-21 1 and Dinotefuran B1-22 1 and Diofenolan B1-23 1 and EmamectinB1-24 1 and Endosulfan B1-25 1 and Esfenvalerate B1-26 1 and EthiproleB1-27 1 and Fenothiocarb B1-28 1 and Fenoxycarb B1-29 1 and FenvalerateB1-30 1 and Fipronil B1-31 1 and Flonicamid B1-32 1 and FlubendiamideB1-33 1 and Flufenoxuron B1-34 1 and Hexaflumuron B1-35 1 andHydramethylnon B1-36 1 and Imidacloprid B1-37 1 and Indoxacarb B1-38 1and Lambda-cyhalothrin B1-39 1 and Lufenuron B1-40 1 and MetaflumizoneB1-41 1 and Methomyl B1-42 1 and Methoprene B1-43 1 and MethoxyfenozideB1-44 1 and Nitenpyram B1-45 1 and Nithiazine B1-46 1 and NovaluronB1-47 1 and Oxamyl B1-48 1 and Phosmet B1-49 1 and Pymetrozine B1-50 1and Pyrethrin B1-51 1 and Pyridaben B1-52 1 and Pyridalyl B1-53 1 andPyriproxyfen B1-54 1 and Ryanodine B1-55 1 and Spinetoram B1-56 1 andSpinosad B1-57 1 and Spirodiclofen B1-58 1 and Spiromesifen B1-59 1 andSpirotetramat B1-60 1 and Tebufenozide B1-61 1 and Thiacloprid B1-62 1and Thiamethoxam B1-63 1 and Thiodicarb B1-64 1 and Thiosultap-sodiumB1-65 1 and Tolfenpyrad B1-66 1 and Tralomethrin B1-67 1 and TriazamateB1-68 1 and Triflumuron B1-69 1 and Bacillus thuringiensis B1-70 1 andBacillus thuringiensis delta-endotoxin B1-71 1 and NPV (e.g., Gemstar)

Table B2

Table B2 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 18. For example, the first mixture in Table B2 is designatedB2-1 and is a mixture of compound 18 and the additional invertebratepest control agent abamectin.

Table B3

Table B3 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 19. For example, the first mixture in Table B3 is designatedB3-1 and is a mixture of compound 19 and the additional invertebratepest control agent abamectin.

Table B4

Table B4 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 20. For example, the first mixture in Table B4 is designatedB4-1 and is a mixture of compound 20 and the additional invertebratepest control agent abamectin.

Table B5

Table B5 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 21. For example, the first mixture in Table B5 is designatedB5-1 and is a mixture of compound 21 and the additional invertebratepest control agent abamectin.

Table B6

Table B6 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 23. For example, the first mixture in Table B6 is designatedB6-1 and is a mixture of compound 23 and the additional invertebratepest control agent abamectin.

Table B7

Table B7 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 26. For example, the first mixture in Table B7 is designatedB7-1 and is a mixture of compound 26 and the additional invertebratepest control agent abamectin.

Table B8

Table B8 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 29. For example, the first mixture in Table B8 is designatedB8-1 and is a mixture of compound 29 and the additional invertebratepest control agent abamectin.

Table B9

Table B9 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 30. For example, the first mixture in Table B9 is designatedB9-1 and is a mixture of compound 30 and the additional invertebratepest control agent abamectin.

Table B10

Table B10 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 33. For example, the first mixture in Table B10 isdesignated B10-1 and is a mixture of compound 33 and the additionalinvertebrate pest control agent abamectin.

Table B11

Table B11 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 36. For example, the first mixture in Table B11 isdesignated B11-1 and is a mixture of compound 36 and the additionalinvertebrate pest control agent abamectin.

Table B12

Table B12 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 37. For example, the first mixture in Table B12 isdesignated B12-1 and is a mixture of compound 37 and the additionalinvertebrate pest control agent abamectin.

Table B13

Table B13 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 40. For example, the first mixture in Table B13 isdesignated B13-1 and is a mixture of compound 40 and the additionalinvertebrate pest control agent abamectin.

Table B14

Table B14 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 44. For example, the first mixture in Table B14 isdesignated B14-1 and is a mixture of compound 44 and the additionalinvertebrate pest control agent abamectin.

Table B15

Table B15 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 47. For example, the first mixture in Table B15 isdesignated B15-1 and is a mixture of compound 47 and the additionalinvertebrate pest control agent abamectin.

Table B16

Table B16 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 49. For example, the first mixture in Table B16 isdesignated B16-1 and is a mixture of compound 49 and the additionalinvertebrate pest control agent abamectin.

Table B17

Table B17 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 50. For example, the first mixture in Table B17 isdesignated B17-1 and is a mixture of compound 50 and the additionalinvertebrate pest control agent abamectin.

Table B18

Table B18 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 51. For example, the first mixture in Table B18 isdesignated B18-1 and is a mixture of compound 51 and the additionalinvertebrate pest control agent abamectin.

Table B19

Table B19 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 52. For example, the first mixture in Table B19 isdesignated B2-1 and is a mixture of compound 52 and the additionalinvertebrate pest control agent abamectin.

Table B20

Table B20 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 53. For example, the first mixture in Table B20 isdesignated B20-1 and is a mixture of compound 53 and the additionalinvertebrate pest control agent abamectin.

Table B21

Table B21 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 56. For example, the first mixture in Table B21 isdesignated B21-1 and is a mixture of compound 56 and the additionalinvertebrate pest control agent abamectin.

Table B22

Table B22 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 57. For example, the first mixture in Table B22 isdesignated B22-1 and is a mixture of compound 57 and the additionalinvertebrate pest control agent abamectin.

Table B23

Table B23 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 58. For example, the first mixture in Table B23 isdesignated B23-1 and is a mixture of compound 58 and the additionalinvertebrate pest control agent abamectin.

Table B24

Table B24 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 59. For example, the first mixture in Table B24 isdesignated B24-1 and is a mixture of compound 59 and the additionalinvertebrate pest control agent abamectin.

Table B25

Table B25 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 60. For example, the first mixture in Table B25 isdesignated B25-1 and is a mixture of compound 60 and the additionalinvertebrate pest control agent abamectin.

Table B26

Table B26 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 62. For example, the first mixture in Table B26 isdesignated B26-1 and is a mixture of compound 62 and the additionalinvertebrate pest control agent abamectin.

Table B27

Table B27 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 63. For example, the first mixture in Table B27 isdesignated B27-1 and is a mixture of compound 63 and the additionalinvertebrate pest control agent abamectin.

Table B28

Table B28 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 65. For example, the first mixture in Table B28 isdesignated B28-1 and is a mixture of compound 65 and the additionalinvertebrate pest control agent abamectin.

Table B29

Table B29 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 71. For example, the first mixture in Table B29 isdesignated B29-1 and is a mixture of compound 71 and the additionalinvertebrate pest control agent abamectin.

Table B30

Table B30 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 74. For example, the first mixture in Table B30 isdesignated B30-1 and is a mixture of compound 74 and the additionalinvertebrate pest control agent abamectin.

Table B31

Table B31 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 77. For example, the first mixture in Table B31 isdesignated B31-1 and is a mixture of compound 77 and the additionalinvertebrate pest control agent abamectin.

Table B32

Table B32 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 79. For example, the first mixture in Table B32 isdesignated B32-1 and is a mixture of compound 79 and the additionalinvertebrate pest control agent abamectin.

Table B33

Table B33 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 80. For example, the first mixture in Table B33 isdesignated B33-1 and is a mixture of compound 80 and the additionalinvertebrate pest control agent abamectin.

Table B34

Table B34 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 81. For example, the first mixture in Table B34 isdesignated B34-1 and is a mixture of compound 81 and the additionalinvertebrate pest control agent abamectin.

Table B35

Table B35 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 82. For example, the first mixture in Table B35 isdesignated B35-1 and is a mixture of compound 82 and the additionalinvertebrate pest control agent abamectin.

Table B36

Table B36 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 83. For example, the first mixture in Table B36 isdesignated B36-1 and is a mixture of compound 83 and the additionalinvertebrate pest control agent abamectin.

Table B37

Table B37 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 84. For example, the first mixture in Table B37 isdesignated B37-1 and is a mixture of compound 84 and the additionalinvertebrate pest control agent abamectin.

Table B38

Table B38 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 85. For example, the first mixture in Table B38 isdesignated B38-1 and is a mixture of compound 85 and the additionalinvertebrate pest control agent abamectin.

Table B39

Table B39 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 86. For example, the first mixture in Table B39 isdesignated B39-1 and is a mixture of compound 86 and the additionalinvertebrate pest control agent abamectin.

Table B40

Table B40 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 87. For example, the first mixture in Table B40 isdesignated B40-1 and is a mixture of compound 87 and the additionalinvertebrate pest control agent abamectin.

Table B41

Table B41 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 89. For example, the first mixture in Table B41 isdesignated B41-1 and is a mixture of compound 89 and the additionalinvertebrate pest control agent abamectin.

Table B42

Table B42 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 99. For example, the first mixture in Table B42 isdesignated B42-1 and is a mixture of compound 99 and the additionalinvertebrate pest control agent abamectin.

Table B43

Table B43 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 102. For example, the first mixture in Table B43 isdesignated B43-1 and is a mixture of compound 102 and the additionalinvertebrate pest control agent abamectin.

Table B44

Table B44 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 113. For example, the first mixture in Table B44 isdesignated B44-1 and is a mixture of compound 113 and the additionalinvertebrate pest control agent abamectin.

Table B45

Table B45 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 118. For example, the first mixture in Table B45 isdesignated B45-1 and is a mixture of compound 118 and the additionalinvertebrate pest control agent abamectin.

Table B46

Table B46 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 125. For example, the first mixture in Table B46 isdesignated B46-1 and is a mixture of compound 125 and the additionalinvertebrate pest control agent abamectin.

Table B47

Table B47 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 137. For example, the first mixture in Table B47 isdesignated B47-1 and is a mixture of compound 137 and the additionalinvertebrate pest control agent abamectin.

Table B48

Table B43 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 183. For example, the first mixture in Table B48 isdesignated B48-1 and is a mixture of compound 183 and the additionalinvertebrate pest control agent abamectin.

Table B49

Table B49 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 190. For example, the first mixture in Table B49 isdesignated B49-1 and is a mixture of compound 190 and the additionalinvertebrate pest control agent abamectin.

Table B50

Table B50 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 191. For example, the first mixture in Table B50 isdesignated B50-1 and is a mixture of compound 191 and the additionalinvertebrate pest control agent abamectin.

Table B51

Table B51 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 196. For example, the first mixture in Table B51 isdesignated B51-1 and is a mixture of compound 196 and the additionalinvertebrate pest control agent abamectin.

Table B52

Table B52 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 229. For example, the first mixture in Table B52 isdesignated B52-1 and is a mixture of compound 229 and the additionalinvertebrate pest control agent abamectin.

Table B53

Table B53 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 231. For example, the first mixture in Table B53 isdesignated B53-1 and is a mixture of compound 231 and the additionalinvertebrate pest control agent abamectin.

Table B54

Table B54 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 254. For example, the first mixture in Table B54 isdesignated B54-1 and is a mixture of compound 254 and the additionalinvertebrate pest control agent abamectin.

Table B55

Table B55 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 257. For example, the first mixture in Table B55 isdesignated B55-1 and is a mixture of compound 257 and the additionalinvertebrate pest control agent abamectin.

Table B56

Table B56 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 272. For example, the first mixture in Table B56 isdesignated B56-1 and is a mixture of compound 272 and the additionalinvertebrate pest control agent abamectin.

Table B57

Table B57 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 289. For example, the first mixture in Table B57 isdesignated B57-1 and is a mixture of compound 289 and the additionalinvertebrate pest control agent abamectin.

Table B58

Table B58 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 296. For example, the first mixture in Table B58 isdesignated B58-1 and is a mixture of compound 296 and the additionalinvertebrate pest control agent abamectin.

Table B59

Table B59 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 299. For example, the first mixture in Table B59 isdesignated B59-1 and is a mixture of compound 299 and the additionalinvertebrate pest control agent abamectin.

Table B60

Table B60 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 307. For example, the first mixture in Table B60 isdesignated B60-1 and is a mixture of compound 307 and the additionalinvertebrate pest control agent abamectin.

Table B61

Table B61 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 308. For example, the first mixture in Table B61 isdesignated B61-1 and is a mixture of compound 308 and the additionalinvertebrate pest control agent abamectin.

Table B62

Table B62 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 315. For example, the first mixture in Table B62 isdesignated B62-1 and is a mixture of compound 315 and the additionalinvertebrate pest control agent abamectin.

Table B63

Table B63 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 343. For example, the first mixture in Table B63 isdesignated B63-1 and is a mixture of compound 343 and the additionalinvertebrate pest control agent abamectin.

Table B64

Table B64 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 344. For example, the first mixture in Table B64 isdesignated B64-1 and is a mixture of compound 344 and the additionalinvertebrate pest control agent abamectin.

Table B65

Table B65 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 352. For example, the first mixture in Table B65 isdesignated B65-1 and is a mixture of compound 352 and the additionalinvertebrate pest control agent abamectin.

Table B66

Table B66 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 363. For example, the first mixture in Table B66 isdesignated B66-1 and is a mixture of compound 363 and the additionalinvertebrate pest control agent abamectin.

Table B67

Table B67 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 364. For example, the first mixture in Table B67 isdesignated B67-1 and is a mixture of compound 364 and the additionalinvertebrate pest control agent abamectin.

Table B68

Table B68 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 368. For example, the first mixture in Table B68 isdesignated B68-1 and is a mixture of compound 368 and the additionalinvertebrate pest control agent abamectin.

Table B69

Table B69 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 381. For example, the first mixture in Table B69 isdesignated B69-1 and is a mixture of compound 381 and the additionalinvertebrate pest control agent abamectin.

Table B70

Table B70 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 385. For example, the first mixture in Table B70 isdesignated B70-1 and is a mixture of compound 385 and the additionalinvertebrate pest control agent abamectin.

Table B71

Table B71 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 421. For example, the first mixture in Table B71 isdesignated B71-1 and is a mixture of compound 421 and the additionalinvertebrate pest control agent abamectin.

Table B72

Table B72 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 433. For example, the first mixture in Table B72 isdesignated B72-1 and is a mixture of compound 433 and the additionalinvertebrate pest control agent abamectin.

Table B73

Table B73 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 435. For example, the first mixture in Table B73 isdesignated B73-1 and is a mixture of compound 435 and the additionalinvertebrate pest control agent abamectin.

Table B74

Table B74 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 448. For example, the first mixture in Table B74 isdesignated B74-1 and is a mixture of compound 448 and the additionalinvertebrate pest control agent abamectin.

Table B75

Table B75 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 449. For example, the first mixture in Table B75 isdesignated B75-1 and is a mixture of compound 449 and the additionalinvertebrate pest control agent abamectin.

Table B76

Table B76 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 450. For example, the first mixture in Table B76 isdesignated B76-1 and is a mixture of compound 450 and the additionalinvertebrate pest control agent abamectin.

Table B77

Table B77 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 451. For example, the first mixture in Table B77 isdesignated B77-1 and is a mixture of compound 451 and the additionalinvertebrate pest control agent abamectin.

Table B78

Table B78 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 462. For example, the first mixture in Table B78 isdesignated B78-1 and is a mixture of compound 462 and the additionalinvertebrate pest control agent abamectin.

Table B79

Table B79 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 482. For example, the first mixture in Table B79 isdesignated B79-1 and is a mixture of compound 482 and the additionalinvertebrate pest control agent abamectin.

Table B80

Table B80 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 490. For example, the first mixture in Table B80 isdesignated B80-1 and is a mixture of compound 490 and the additionalinvertebrate pest control agent abamectin.

Table B81

Table B81 is identical to Table B1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 493. For example, the first mixture in Table B81 isdesignated B81-1 and is a mixture of compound 493 and the additionalinvertebrate pest control agent abamectin.

The specific mixtures listed in Tables B1 to B81 typically combine acompound of Formula 1 with the other invertebrate pest agent in theratios specified in Table A.

Listed below in Tables C1 to C81 are embodiments of specificcompositions comprising a compound of Formula 1 (compound numbers (Cmpd.No.) refer to compounds in Index Tables A-E) and an additionalfungicide.

TABLE C1 Mixture Cmpd. No. No. and Fungicide C1-1 1 and Probenazole C1-21 and Tiadinil C1-3 1 and Isotianil C1-4 1 and Pyroquilon C1-5 1 andMetominostrobin C1-6 1 and Flutolanil C1-7 1 and Validamycin C1-8 1 andFurametpyr C1-9 1 and Pencycuron C1-10 1 and Simeconazole C1-11 1 andOrysastrobin C1-12 1 and Trifloxystrobin C1-13 1 and IsoprothiolaneC1-14 1 and Azoxystrobin C1-15 1 and Tricyclazole C1-16 1 andHexaconazole C1-17 1 and Difenoconazole C1-18 1 and Cyproconazole C1-191 and Propiconazole C1-20 1 and Fenoxanil C1-21 1 and Ferimzone C1-22 1and Fthalide C1-23 1 and Kasugamycin C1-24 1 and Picoxystrobin C1-25 1and Penthiopyrad C1-26 1 and Famoxadone C1-27 1 and Cymoxanil C1-28 1and Proquinazid C1-29 1 and Flusilazole C1-30 1 and Mancozeb C1-31 1 andCopper hydroxide C1-32 1 and (a) (a)1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone

Table C2

Table C2 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 18. For example, the first mixture in Table C2 is designatedC2-1 and is a mixture of compound 18 and the additional fungicideprobenazole.

Table C3

Table C3 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 19. For example, the first mixture in Table C3 is designatedC3-1 and is a mixture of compound 19 and the additional fungicideprobenazole.

Table C4

Table C4 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 20. For example, the first mixture in Table C4 is designatedC4-1 and is a mixture of compound 20 and the additional fungicideprobenazole.

Table C5

Table C5 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 21. For example, the first mixture in Table C5 is designatedC5-1 and is a mixture of compound 21 and the additional fungicideprobenazole.

Table C6

Table C6 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 23. For example, the first mixture in Table C6 is designatedC6-1 and is a mixture of compound 23 and the additional fungicideprobenazole.

Table C7

Table C7 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 26. For example, the first mixture in Table C7 is designatedC7-1 and is a mixture of compound 26 and the additional fungicideprobenazole.

Table C8

Table C8 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 29. For example, the first mixture in Table C8 is designatedC8-1 and is a mixture of compound 29 and the additional fungicideprobenazole.

Table C9

Table C9 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 30. For example, the first mixture in Table C9 is designatedC9-1 and is a mixture of compound 30 and the additional fungicideprobenazole.

Table C10

Table C10 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 33. For example, the first mixture in Table C10 isdesignated C10-1 and is a mixture of compound 33 and the additionalfungicide probenazole.

Table C11

Table C11 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 36. For example, the first mixture in Table C11 isdesignated C11-1 and is a mixture of compound 36 and the additionalfungicide probenazole.

Table C12

Table C12 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 37. For example, the first mixture in Table C12 isdesignated C12-1 and is a mixture of compound 37 and the additionalfungicide probenazole.

Table C13

Table C13 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 40. For example, the first mixture in Table C13 isdesignated C13-1 and is a mixture of compound 40 and the additionalfungicide probenazole.

Table C14

Table C14 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 44. For example, the first mixture in Table C14 isdesignated C14-1 and is a mixture of compound 44 and the additionalfungicide probenazole.

Table C15

Table C15 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 47. For example, the first mixture in Table C15 isdesignated C15-1 and is a mixture of compound 47 and the additionalfungicide probenazole.

Table C16

Table C16 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 49. For example, the first mixture in Table C16 isdesignated C16-1 and is a mixture of compound 49 and the additionalfungicide probenazole.

Table C17

Table C17 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 50. For example, the first mixture in Table C17 isdesignated C17-1 and is a mixture of compound 50 and the additionalfungicide probenazole.

Table C18

Table C18 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 51. For example, the first mixture in Table C18 isdesignated C18-1 and is a mixture of compound 51 and the additionalfungicide probenazole.

Table C19

Table C19 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 52. For example, the first mixture in Table C19 isdesignated C19-1 and is a mixture of compound 52 and the additionalfungicide probenazole.

Table C20

Table C20 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 53. For example, the first mixture in Table C20 isdesignated C20-1 and is a mixture of compound 53 and the additionalfungicide probenazole.

Table C21

Table C21 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 56. For example, the first mixture in Table C21 isdesignated C21-1 and is a mixture of compound 56 and the additionalfungicide probenazole.

Table C22

Table C22 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 57. For example, the first mixture in Table C22 isdesignated C22-1 and is a mixture of compound 57 and the additionalfungicide probenazole.

Table C23

Table C23 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 58. For example, the first mixture in Table C23 isdesignated C23-1 and is a mixture of compound 58 and the additionalfungicide probenazole.

Table C24

Table C24 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 59. For example, the first mixture in Table C24 isdesignated C24-1 and is a mixture of compound 59 and the additionalfungicide probenazole.

Table C25

Table C25 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 60. For example, the first mixture in Table C25 isdesignated C25-1 and is a mixture of compound 60 and the additionalfungicide probenazole.

Table C26

Table C26 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 62. For example, the first mixture in Table C26 isdesignated C26-1 and is a mixture of compound 62 and the additionalfungicide probenazole.

Table C27

Table C27 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 63. For example, the first mixture in Table C27 isdesignated C27-1 and is a mixture of compound 63 and the additionalfungicide probenazole.

Table C28

Table C28 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 65. For example, the first mixture in Table C28 isdesignated C28-1 and is a mixture of compound 65 and the additionalfungicide probenazole.

Table C29

Table C29 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 71. For example, the first mixture in Table C29 isdesignated C29-1 and is a mixture of compound 71 and the additionalfungicide probenazole.

Table C30

Table C30 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 74. For example, the first mixture in Table C30 isdesignated C30-1 and is a mixture of compound 74 and the additionalfungicide probenazole.

Table C31

Table C31 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 77. For example, the first mixture in Table C31 isdesignated C31-1 and is a mixture of compound 77 and the additionalfungicide probenazole.

Table C32

Table C32 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 79. For example, the first mixture in Table C32 isdesignated C32-1 and is a mixture of compound 79 and the additionalfungicide probenazole.

Table C33

Table C33 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 80. For example, the first mixture in Table C33 isdesignated C33-1 and is a mixture of compound 80 and the additionalfungicide probenazole.

Table C34

Table C34 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 81. For example, the first mixture in Table C34 isdesignated C34-1 and is a mixture of compound 81 and the additionalfungicide probenazole.

Table C35

Table C35 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 82. For example, the first mixture in Table C35 isdesignated C35-1 and is a mixture of compound 82 and the additionalfungicide probenazole.

Table C36

Table C36 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 83. For example, the first mixture in Table C36 isdesignated C36-1 and is a mixture of compound 83 and the additionalfungicide probenazole.

Table C37

Table C37 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 84. For example, the first mixture in Table C37 isdesignated C37-1 and is a mixture of compound 84 and the additionalfungicide probenazole.

Table C38

Table C38 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 85. For example, the first mixture in Table C38 isdesignated C38-1 and is a mixture of compound 85 and the additionalfungicide probenazole.

Table C39

Table C39 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 86. For example, the first mixture in Table C39 isdesignated C39-1 and is a mixture of compound 86 and the additionalfungicide probenazole.

Table C40

Table C40 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 87. For example, the first mixture in Table C40 isdesignated C40-1 and is a mixture of compound 87 and the additionalfungicide probenazole.

Table C41

Table C41 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 89. For example, the first mixture in Table C41 isdesignated C41-1 and is a mixture of compound 89 and the additionalfungicide probenazole.

Table C42

Table C42 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 99. For example, the first mixture in Table C42 isdesignated C42-1 and is a mixture of compound 99 and the additionalfungicide probenazole.

Table C43

Table C43 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 102. For example, the first mixture in Table C43 isdesignated C43-1 and is a mixture of compound 102 and the additionalfungicide probenazole.

Table C44

Table C44 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 113. For example, the first mixture in Table C44 isdesignated C44-1 and is a mixture of compound 113 and the additionalfungicide probenazole.

Table C45

Table C45 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 118. For example, the first mixture in Table C45 isdesignated C45-1 and is a mixture of compound 118 and the additionalfungicide probenazole.

Table C46

Table C46 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 125. For example, the first mixture in Table C46 isdesignated C46-1 and is a mixture of compound 125 and the additionalfungicide probenazole.

Table C47

Table C47 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 137. For example, the first mixture in Table C47 isdesignated C47-1 and is a mixture of compound 137 and the additionalfungicide probenazole.

Table C48

Table C43 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 183. For example, the first mixture in Table C48 isdesignated C48-1 and is a mixture of compound 183 and the additionalfungicide probenazole.

Table C49

Table C49 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 190. For example, the first mixture in Table C49 isdesignated C49-1 and is a mixture of compound 190 and the additionalfungicide probenazole.

Table C50

Table C50 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 191. For example, the first mixture in Table C50 isdesignated C50-1 and is a mixture of compound 191 and the additionalfungicide probenazole.

Table C51

Table C51 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 196. For example, the first mixture in Table C51 isdesignated C51-1 and is a mixture of compound 196 and the additionalfungicide probenazole.

Table C52

Table C52 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 229. For example, the first mixture in Table C52 isdesignated C52-1 and is a mixture of compound 229 and the additionalfungicide probenazole.

Table C53

Table C53 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 231. For example, the first mixture in Table C53 isdesignated C53-1 and is a mixture of compound 231 and the additionalfungicide probenazole.

Table C54

Table C54 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 254. For example, the first mixture in Table C54 isdesignated C54-1 and is a mixture of compound 254 and the additionalfungicide probenazole.

Table C55

Table C55 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 257. For example, the first mixture in Table C55 isdesignated C55-1 and is a mixture of compound 257 and the additionalfungicide probenazole.

Table C56

Table C56 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 272. For example, the first mixture in Table C56 isdesignated C56-1 and is a mixture of compound 272 and the additionalfungicide probenazole.

Table C57

Table C57 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 289. For example, the first mixture in Table C57 isdesignated C57-1 and is a mixture of compound 289 and the additionalfungicide probenazole.

Table C58

Table C58 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 296. For example, the first mixture in Table C58 isdesignated C58-1 and is a mixture of compound 296 and the additionalfungicide probenazole.

Table C59

Table C59 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 299. For example, the first mixture in Table C59 isdesignated C59-1 and is a mixture of compound 299 and the additionalfungicide probenazole.

Table C60

Table C60 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 307. For example, the first mixture in Table C60 isdesignated C60-1 and is a mixture of compound 307 and the additionalfungicide probenazole.

Table C61

Table C61 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 308. For example, the first mixture in Table C61 isdesignated C61-1 and is a mixture of compound 308 and the additionalfungicide probenazole.

Table C62

Table C62 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 315. For example, the first mixture in Table C62 isdesignated C62-1 and is a mixture of compound 315 and the additionalfungicide probenazole.

Table C63

Table C63 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 343. For example, the first mixture in Table C63 isdesignated C63-1 and is a mixture of compound 343 and the additionalfungicide probenazole.

Table C64

Table C64 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 344. For example, the first mixture in Table C64 isdesignated C64-1 and is a mixture of compound 344 and the additionalfungicide probenazole.

Table C65

Table C65 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 352. For example, the first mixture in Table C65 isdesignated C65-1 and is a mixture of compound 352 and the additionalfungicide probenazole.

Table C66

Table C66 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 363. For example, the first mixture in Table C66 isdesignated C66-1 and is a mixture of compound 363 and the additionalfungicide probenazole.

Table C67

Table C67 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 364. For example, the first mixture in Table C67 isdesignated C67-1 and is a mixture of compound 364 and the additionalfungicide probenazole.

Table C68

Table C68 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 368. For example, the first mixture in Table C68 isdesignated C68-1 and is a mixture of compound 368 and the additionalfungicide probenazole.

Table C69

Table C69 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 381. For example, the first mixture in Table C69 isdesignated C69-1 and is a mixture of compound 381 and the additionalfungicide probenazole.

Table C70

Table C70 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 385. For example, the first mixture in Table C70 isdesignated C70-1 and is a mixture of compound 385 and the additionalfungicide probenazole.

Table C71

Table C71 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 421. For example, the first mixture in Table C71 isdesignated C71-1 and is a mixture of compound 421 and the additionalfungicide probenazole.

Table C72

Table C72 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 433. For example, the first mixture in Table C72 isdesignated C72-1 and is a mixture of compound 433 and the additionalfungicide probenazole.

Table C73

Table C73 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 435. For example, the first mixture in Table C73 isdesignated C73-1 and is a mixture of compound 435 and the additionalfungicide probenazole.

Table C74

Table C74 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 448. For example, the first mixture in Table C74 isdesignated C74-1 and is a mixture of compound 448 and the additionalfungicide probenazole.

Table C75

Table C75 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 449. For example, the first mixture in Table C75 isdesignated C75-1 and is a mixture of compound 449 and the additionalfungicide probenazole.

Table C76

Table C76 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 450. For example, the first mixture in Table C76 isdesignated C76-1 and is a mixture of compound 450 and the additionalfungicide probenazole.

Table C77

Table C77 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 451. For example, the first mixture in Table C77 isdesignated C77-1 and is a mixture of compound 451 and the additionalfungicide probenazole.

Table C78

Table C78 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 462. For example, the first mixture in Table C78 isdesignated C78-1 and is a mixture of compound 462 and the additionalfungicide probenazole.

Table C79

Table C79 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 482. For example, the first mixture in Table C79 isdesignated C79-1 and is a mixture of compound 482 and the additionalfungicide probenazole.

Table C80

Table C80 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 490. For example, the first mixture in Table C80 isdesignated C80-1 and is a mixture of compound 490 and the additionalfungicide probenazole.

Table C81

Table C81 is identical to Table C1, except that each reference tocompound 1 in the column headed “Cmpd. No.” is replaced by a referenceto compound 493. For example, the first mixture in Table C81 isdesignated C81-1 and is a mixture of compound 493 and the additionalfungicide probenazole.

Invertebrate pests are controlled in agronomic and nonagronomicapplications by applying one or more compounds of this invention,typically in the form of a composition, in a biologically effectiveamount, to the environment of the pests, including the agronomic and/ornonagronomic locus of infestation, to the area to be protected, ordirectly on the pests to be controlled.

Thus the present invention comprises a method for controlling aninvertebrate pest in agronomic and/or nonagronomic applications,comprising contacting the invertebrate pest or its environment with abiologically effective amount of one or more of the compounds of theinvention, or with a composition comprising at least one such compoundor a composition comprising at least one such compound and abiologically effective amount of at least one additional biologicallyactive compound or agent. Examples of suitable compositions comprising acompound of the invention and a biologically effective amount of atleast one additional biologically active compound or agent includegranular compositions wherein the additional active compound is presenton the same granule as the compound of the invention or on granulesseparate from those of the compound of the invention.

Embodiments of the method of this invention include contacting theenvironment. Of note is the method wherein the environment is a plant.Also of note is the method wherein the environment is an animal. Also ofnote is the method wherein the environment is a seed.

To achieve contact with a compound or composition of the invention toprotect a field crop from invertebrate pests, the compound orcomposition is typically applied to the seed of the crop beforeplanting, to the foliage (e.g., leaves, stems, flowers, fruits) of cropplants, or to the soil or other growth medium before or after the cropis planted.

One embodiment of a method of contact is by spraying. Alternatively, agranular composition comprising a compound of the invention can beapplied to the plant foliage or the soil. Compounds of this inventioncan also be effectively delivered through plant uptake by contacting theplant with a composition comprising a compound of this invention appliedas a soil drench of a liquid formulation, a granular formulation to thesoil, a nursery box treatment or a dip of transplants. Of note is acomposition of the present invention in the form of a soil drench liquidformulation. Also of note is a method for controlling an invertebratepest comprising contacting the invertebrate pest or its environment witha biologically effective amount of a compound of the present inventionor with a composition comprising a biologically effective amount of acompound of the present invention. Of further note is this methodwherein the environment is soil and the composition is applied to thesoil as a soil drench formulation. Of further note is that compounds ofthis invention are also effective by localized application to the locusof infestation. Other methods of contact include application of acompound or a composition of the invention by direct and residualsprays, aerial sprays, gels, seed coatings, microencapsulations,systemic uptake, baits, ear tags, boluses, foggers, fumigants, aerosols,dusts and many others. One embodiment of a method of contact is adimensionally stable fertilizer granule, stick or tablet comprising acompound or composition of the invention. The compounds of thisinvention can also be impregnated into materials for fabricatinginvertebrate control devices (e.g., insect netting).

Compounds of this invention are also useful in seed treatments forprotecting seeds from invertebrate pests. In the context of the presentdisclosure and claims, treating a seed means contacting the seed with abiologically effective amount of a compound of this invention, which istypically formulated as a composition of the invention. This seedtreatment protects the seed from invertebrate soil pests and generallycan also protect roots and other plant parts in contact with the soil ofthe seedling developing from the germinating seed. The seed treatmentmay also provide protection of foliage by translocation of the compoundof this invention or a second active ingredient within the developingplant. Seed treatments can be applied to all types of seeds, includingthose from which plants genetically transformed to express specializedtraits will germinate. Representative examples include those expressingproteins toxic to invertebrate pests, such as Bacillus thuringiensistoxin or those expressing herbicide resistance such as glyphosateacetyltransferase, which provides resistance to glyphosate.

One method of seed treatment is by spraying or dusting the seed with acompound of the invention (i.e. as a formulated composition) beforesowing the seeds. Compositions formulated for seed treatment generallycomprise a film former or adhesive agent. Therefore typically a seedcoating composition of the present invention comprises a biologicallyeffective amount of a compound of Formula 1, an N-oxide, or saltthereof, and a film former or adhesive agent. Seed can be coated byspraying a flowable suspension concentrate directly into a tumbling bedof seeds and then drying the seeds. Alternatively, other formulationtypes such as wetted powders, solutions, suspoemulsions, emulsifiableconcentrates and emulsions in water can be sprayed on the seed. Thisprocess is particularly useful for applying film coatings on seeds.Various coating machines and processes are available to one skilled inthe art. Suitable processes include those listed in P. Kosters et al.,Seed Treatment: Progress and Prospects, 1994 BCPC Mongraph No. 57, andreferences listed therein.

The treated seed typically comprises a compound of the present inventionin an amount from about 0.1 g to 1 kg per 100 kg of seed (i.e. fromabout 0.0001 to 1% by weight of the seed before treatment). A flowablesuspension formulated for seed treatment typically comprises from about0.5 to about 70% of the active ingredient, from about 0.5 to about 30%of a film-forming adhesive, from about 0.5 to about 20% of a dispersingagent, from 0 to about 5% of a thickener, from 0 to about 5% of apigment and/or dye, from 0 to about 2% of an antifoaming agent, from 0to about 1% of a preservative, and from 0 to about 75% of a volatileliquid diluent.

The compounds of this invention can be incorporated into a baitcomposition that is consumed by an invertebrate pest or used within adevice such as a trap, bait station, and the like. Such a baitcomposition can be in the form of granules which comprise (a) activeingredients, namely a biologically effective amount of a compound ofFormula 1 an N-oxide, or salt thereof; (b) one or more food materials;optionally (c) an attractant, and optionally (d) one or more humectants.Of note are granules or bait compositions which comprise between about0.001-5% active ingredients, about 40-99% food material and/orattractant; and optionally about 0.05-10% humectants, which areeffective in controlling soil invertebrate pests at very low applicationrates, particularly at doses of active ingredient that are lethal byingestion rather than by direct contact. Some food materials canfunction both as a food source and an attractant. Food materials includecarbohydrates, proteins and lipids. Examples of food materials arevegetable flour, sugar, starches, animal fat, vegetable oil, yeastextracts and milk solids. Examples of attractants are odorants andflavorants, such as fruit or plant extracts, perfume, or other animal orplant component, pheromones or other agents known to attract a targetinvertebrate pest. Examples of humectants, i.e. moisture retainingagents, are glycols and other polyols, glycerine and sorbitol. Of noteis a bait composition (and a method utilizing such a bait composition)used to control at least one invertebrate pest selected from the groupconsisting of ants, termites and cockroaches. A device for controllingan invertebrate pest can comprise the present bait composition and ahousing adapted to receive the bait composition, wherein the housing hasat least one opening sized to permit the invertebrate pest to passthrough the opening so the invertebrate pest can gain access to the baitcomposition from a location outside the housing, and wherein the housingis further adapted to be placed in or near a locus of potential or knownactivity for the invertebrate pest.

The compounds of this invention can be applied without other adjuvants,but most often application will be of a formulation comprising one ormore active ingredients with suitable carriers, diluents, andsurfactants and possibly in combination with a food depending on thecontemplated end use. One method of application involves spraying awater dispersion or refined oil solution of a compound of the presentinvention. Combinations with spray oils, spray oil concentrations,spreader stickers, adjuvants, other solvents, and synergists such aspiperonyl butoxide often enhance compound efficacy. For nonagronomicuses such sprays can be applied from spray containers such as a can, abottle or other container, either by means of a pump or by releasing itfrom a pressurized container, e.g., a pressurized aerosol spray can.Such spray compositions can take various forms, for example, sprays,mists, foams, fumes or fog. Such spray compositions thus can furthercomprise propellants, foaming agents, etc. as needed for application. Ofnote is a spray composition comprising a biologically effective amountof a compound or a composition of the present invention and a carrier.One embodiment of such a spray composition comprises a biologicallyeffective amount of a compound or a composition of the present inventionand a propellant. Representative propellants include, but are notlimited to, methane, ethane, propane, butane, isobutane, butene,pentane, isopentane, neopentane, pentene, hydrofluorocarbons,chlorofluorocarbons, dimethyl ether, and mixtures of the foregoing. Ofnote is a spray composition (and a method utilizing such a spraycomposition dispensed from a spray container) used to control at leastone invertebrate pest selected from the group consisting of mosquitoes,black flies, stable flies, deer flies, horse flies, wasps, yellowjackets, hornets, ticks, spiders, ants, gnats, and the like, includingindividually or in combinations.

Nonagronomic uses refer to invertebrate pest control in the areas otherthan fields of crop plants. Nonagronomic uses of the present compoundsand compositions include control of invertebrate pests in stored grains,beans and other foodstuffs, and in textiles such as clothing andcarpets. Nonagronomic uses of the present compounds and compositionsalso include invertebrate pest control in ornamental plants, forests, inyards, along roadsides and railroad rights of way, and on turf such aslawns, golf courses and pastures. Nonagronomic uses of the presentcompounds and compositions also include invertebrate pest control inhouses and other buildings which may be occupied by humans and/orcompanion, farm, ranch, zoo or other animals. Nonagronomic uses of thepresent compounds and compositions also include the control of pestssuch as termites that can damage wood or other structural materials usedin buildings.

Nonagronomic uses of the present compounds and compositions also includeprotecting human and animal health by controlling invertebrate peststhat are parasitic or transmit infectious diseases. The controlling ofanimal parasites includes controlling external parasites that areparasitic to the surface of the body of the host animal (e.g.,shoulders, armpits, abdomen, inner part of the thighs) and internalparasites that are parasitic to the inside of the body of the hostanimal (e.g., stomach, intestine, lung, veins, under the skin, lymphatictissue). External parasitic or disease transmitting pests include, forexample, chiggers, ticks, lice, mosquitoes, flies, mites and fleas.Internal parasites include heartworms, hookworms and helminths.Compounds and compositions of the present invention are particularlysuitable for combating external parasitic or disease transmitting pests.Compounds and compositions of the present invention are suitable forsystemic and/or non-systemic control of infestation or infection byparasites on animals.

Compounds and compositions of the present invention are suitable forcombating parasites that infest animal subjects including those in thewild, livestock and agricultural working animals such as cattle, sheep,goats, horses, pigs, donkeys, camels, bison, buffalos, rabbits, hens,turkeys, ducks, geese and bees (e.g., raised for meat, milk, butter,eggs, fur, leather, feathers and/or wool). By combating parasites,fatalities and performance reduction (in terms of meat, milk, wool,skins, eggs, honey, etc.) are reduced, so that applying a compositioncomprising a compound of the present invention allows more economic andsimple husbandry of animals.

Compounds and compositions of the present invention are especiallysuitable for combating parasites that infest companion animals and pets(e.g., dogs, cats, pet birds and aquarium fish), research andexperimental animals (e.g., hamsters, guinea pigs, rats and mice), aswell as animals raised for/in zoos, wild habitats and/or circuses.

In an embodiment of this invention, the animal is preferably avertebrate, and more preferably a mammal, avian or fish. In a particularembodiment, the animal subject is a mammal (including great apes, suchas humans). Other mammalian subjects include primates (e.g., monkeys),bovine (e.g., cattle or dairy cows), porcine (e.g., hogs or pigs), ovine(e.g., goats or sheep), equine (e.g., horses), canine (e.g., dogs),feline (e.g., house cats), camels, deer, donkeys, bison, buffalos,antelopes, rabbits, and rodents (e.g., guinea pigs, squirrels, rats,mice, gerbils, and hamsters). Avians include Anatidae (swans, ducks andgeese), Columbidae (e.g., doves and pigeons), Phasianidae (e.g.,partridges, grouse and turkeys), Thesienidae (e.g., domestic chickens),Psittacines (e.g., parakeets, macaws, and parrots), game birds, andratites (e.g., ostriches).

Birds treated or protected by the inventive compounds can be associatedwith either commercial or noncommercial aviculture. These includeAnatidae, such as swans, geese, and ducks, Columbidae, such as doves anddomestic pigeons, Phasianidae, such as partridge, grouse and turkeys,Thesienidae, such as domestic chickens, and Psittacines, such asparakeets, macaws, and parrots raised for the pet or collector market,among others.

For purposes of the present invention, the term “fish” shall beunderstood to include without limitation, the Teleosti grouping of fish,i.e., teleosts. Both the Salmoniformes order (which includes theSalmonidae family) and the Perciformes order (which includes theCentrarchidae family) are contained within the Teleosti grouping.Examples of potential fish recipients include the Salmonidae,Serranidae, Sparidae, Cichlidae, and Centrarchidae, among others.

Other animals are also contemplated to benefit from the inventivemethods, including marsupials (such as kangaroos), reptiles (such asfarmed turtles), and other economically important domestic animals forwhich the inventive methods are safe and effective in treating orpreventing parasite infection or infestation.

Examples of invertebrate parasitic pests controlled by administering aparasiticidally effective amount of a compound of this invention to ananimal to be protected include ectoparasites (arthropods, acarines, etc)and endoparasites (helminths, e.g., nematodes, trematodes, cestodes,acanthocephalans, etc.).

The disease or group of diseases described generally as helminthiasis isdue to infection of an animal host with parasitic worms known ashelminths. The term ‘helminths’ is meant to include nematodes,trematodes, cestodes and acanthocephalans. Helminthiasis is a prevalentand serious economic problem with domesticated animals such as swine,sheep, horses, cattle, goats, dogs, cats and poultry.

Among the Helminths, the group of worms described as nematodes causeswidespread and at times serious infection in various species of animals.Nematodes that are contemplated to be treated by the compounds of thisinvention and by the inventive methods include, without limitation, thefollowing genera: Acanthocheilonema, Aelurostrongylus, Ancylostoma,Angiostrongylus, Ascaridia, Ascaris, Brugia, Bunostomum, Capillaria,Chabertia, Cooperia, Crenosoma, Dictyocaulus, Dioctophyme, Dipetalonema,Diphyllobothrium, Dirofilaria, Dracunculus, Enterobius, Filaroides,Haemonchus, Heterakis, Lagochilascaris, Loa, Mansonella, Muellerius,Necator, Nematodirus, Oesophagostomum, Ostertagia, Oxyuris, Parafilaria,Parascaris, Physaloptera, Protostrongylus, Setaria, Spirocerca,Stephanofilaria, Strongyloides, Strongylus, Thelazia, Toxascaris,Toxocara, Trichinella, Trichonema, Trichostrongylus, Trichuris,Uncinaria and Wuchereria.

Of the above, the most common genera of nematodes infecting the animalsreferred to above are Haemonchus, Trichostrongylus, Ostertagia,Nematodirus, Cooperia, Ascaris, Bunostomum, Oesophagostomum, Chabertia,Trichuris, Strongylus, Trichonema, Dictyocaulus, Capillaria, Heterakis,Toxocara, Ascaridia, Oxyuris, Ancylostoma, Uncinaria, Toxascaris andParascaris. Certain of these, such as Nematodirus, Cooperia andOesophagostomum attack primarily the intestinal tract while others, suchas Haemonchus and Ostertagia, are more prevalent in the stomach whileothers such as Dictyocaulus are found in the lungs. Still otherparasites may be located in other tissues such as the heart and bloodvessels, subcutaneous and lymphatic tissue and the like.

Trematodes that are contemplated to be treated by the compounds of thisinvention and by the inventive methods include, without limitation, thefollowing genera: Alaria, Fasciola, Nanophyetus, Opisthorchis,Paragonimus and Schistosoma.

Cestodes that are contemplated to be treated by the compounds of thisinvention and by the inventive methods include, without limitation, thefollowing genera: Diphyllobothrium, Diplydium, Spirometra and Taenia.

The most common genera of parasites of the gastrointestinal tract ofhumans are Ancylostoma, Necator, Ascaris, Strongyloides, Trichinella,Capillaria, Trichuris and Enterobius. Other medically important generaof parasites which are found in the blood or other tissues and organsoutside the gastrointestinal tract are the filarial worms such asWuchereria, Brugia, Onchocerca and Loa, as well as Dracunculus and extraintestinal stages of the intestinal worms Strongyloides and Trichinella.

Numerous other Helminth genera and species are known to the art, and arealso contemplated to be treated by the compounds of the invention. Theseare enumerated in great detail in Textbook of Veterinary ClinicalParasitology, Volume 1, Helminths, E. J. L. Soulsby, F. A. Davis Co.,Philadelphia, Pa.; Helminths, Arthropods and Protozoa, (6^(th) Editionof Monnig's Veterinary Helminthology and Entomology), E. J. L. Soulsby,The Williams and Wilkins Co., Baltimore, Md.

It is also contemplated that the inventive compounds are effectiveagainst a number of ectoparasites of animals, e.g., arthropodectoparasites of mammals and birds although it is also recognized thatsome arthropods can be endoparasites as well.

Thus, insect and acarine pests include, e.g., biting insects, such asflies and mosquitoes, mites, ticks, lice, fleas, true bugs, parasiticmaggots, and the like.

Adult flies include, e.g., the horn fly or Haematobia irritans, thehorse fly or Tabanus spp., the stable fly or Stomoxys calcitrans, theblack fly or Simulium spp., the deer fly or Chrysops spp., the louse flyor Melophagus ovinus, the tsetse fly or Glossina spp. Parasitic flymaggots include, e.g., the bot fly (Oestrus ovis and Cuterebra spp.),the blow fly or Phaenicia spp., the screwworm or Cochliomyiahominivorax, the cattle grub or Hypoderma spp., the fleeceworm and theGastrophilus of horses. Mosquitoes include, for example, Culex spp.,Anopheles spp., and Aedes spp.

Mites include Mesostigmata spp. e.g., mesostigmatids such as the chickenmite, Dermanyssus gallinae; itch or scab mites such as Sarcoptidae spp.for example, Sarcoptes scabiei; mange mites such as Psoroptidae spp.including Chorioptes bovis and Psoroptes ovis; chiggers e.g.,Trombiculidae spp. for example the North American chigger, Trombiculaalfreddugesi.

Ticks include, e.g., soft-bodied ticks including Argasidae spp. forexample Argas spp. and Ornithodoros spp.; hard-bodied ticks includingIxodidae spp., for example Rhipicephalus sanguineus, Dermacentorvariabilis, Dermacentor andersoni, Amblyomma americanum, Ixodesscapularis and Boophilus spp.

Lice include, e.g., sucking lice, e.g., Menopon spp. and Bovicola spp.;biting lice, e.g., Haematopinus spp., Linognathus spp. and Solenopotesspp.

Fleas include, e.g., Ctenocephalides spp., such as dog flea(Ctenocephalides canis) and cat flea (Ctenocephalides felis); Xenopsyllaspp. such as oriental rat flea (Xenopsylla cheopis); and Pulex spp. suchas human flea (Pulex irritans).

True bugs include, e.g., Cimicidae or e.g., the common bed bug (Cimexlectularius); Triatominae spp. including triatomid bugs also known askissing bugs; for example Rhodnius prolixus and Triatoma spp.

-   Generally, flies, fleas, lice, mosquitoes, gnats, mites, ticks and    helminths cause tremendous losses to the livestock and companion    animal sectors. Arthropod parasites also are a nuisance to humans    and can vector disease-causing organisms in humans and animals.

Numerous other arthropod pests and ectoparasites are known to the art,and are also contemplated to be treated by the compounds of theinvention. These are enumerated in great detail in Medical andVeterinary Entomology, D. S. Kettle, John Wiley & Sons, New York andToronto; Control of Arthropod Pests of Livestock: A Review ofTechnology, R. O. Drummand, J. E. George, and S. E. Kunz, CRC Press,Boca Raton, Fla.

The compounds and compositions of this invention may also be effectiveagainst a number of protozoa endoparasites of animals, such as thosesummarized by Table 1, as follows.

TABLE 1 Exemplary Parasitic Protozoa and Associated Human DiseasesRepresentative Human Disease Phylum Subphylum Genera or DisorderSarcomastigophora Mastigophora Leishmania Visceral, (with flagella,(Flagella) cutaneous and pseudopodia, or mucocutaneous both) InfectionTrypansoma Sleeping sickness Chagas' disease Giardia DiarrheaTrichomonas Vaginitis Sarcodina Entamoeba Dysentery, (pseudopodia) liverAbscess Dientamoeba Colitis Naegleria and Central Acanthamoeba nervoussystem and corneal ulcers Babesia Babesiesis Apicomplexa PlasmodiumMalaria (apical complex) Isospora Diarrhea Sarcocystis DiarrheaCryptosporidum Diarrhea Toxoplasma Toxoplasmosis Eimeria Chickencoccidiosis Microspora Enterocytozoon Diarrhea Ciliaphora (withBalantidium Dysentery cilia) Unclassified Pneumocystis Pneumonia

In particular, the compounds of this invention are effective againstectoparasites including fleas such as Ctenocephalides felis (cat flea)and Ctenocephalides canis (dog flea).

The compounds of this invention may also be effective against otherectoparasites including flies such as Haematobia (Lyperosia) irritans(horn fly), Stomoxys calcitrans (stable fly), Simulium spp. (blackfly),Glossina spp. (tsetse flies), Hydrotaea irritans (head fly), Muscaautumnalis (face fly), Musca domestica (house fly), Morellia simplex(sweat fly), Tabanus spp. (horse fly), Hypoderma bovis, Hypodermalineatum, Lucilia sericata, Lucilia cuprina (green blowfly), Calliphoraspp. (blowfly), Protophormia spp., Oestrus ovis (nasal botfly),Culicoides spp. (midges), Hippobosca equine, Gastrophilus instestinalis,Gastrophilus haemorrhoidalis and Gastrophilus naslis; lice such asBovicola (Damalinia) bovis, Bovicola equi, Haematopinus asini, Felicolasubrostratus, Heterodoxus spiniger, Lignonathus setosus and Trichodectescanis; keds such as Melophagus ovinus; mites such as Psoroptes spp.,Sarcoptes scabei, Chorioptes bovis, Demodex equi, Cheyletiella spp.,Notoedres cati, Trombicula spp. and Otodectes cyanotis (ear mites); andticks such as Ixodes spp., Boophilus spp., Rhipicephalus spp., Amblyommaspp., Dermacentor spp., Hyalomma spp. and Haemaphysalis spp.

Biologically active compounds or agents useful in the compositions ofthe present invention include the organophosphate pesticides. This classof pesticides has very broad activity as insecticides and, in certaininstances, anthelmintic activity. Organophosphate pesticides include,e.g., dicrotophos, terbufos, dimethoate, diazinon, disulfoton,trichlorfon, azinphos-methyl, chlorpyrifos, malathion,oxydemeton-methyl, methamidophos, acephate, ethyl parathion, methylparathion, mevinphos, phorate, carbofenthion and phosalone. It is alsocontemplated to include combinations of the inventive methods andcompounds with carbamate type pesticides, including, e.g., carbaryl,carbofuran, aldicarb, molinate, methomyl, carbofuran, etc., as well ascombinations with the organochlorine type pesticides. It is furthercontemplated to include combinations with biological pesticides,including repellents, the pyrethrins (as well as synthetic variationsthereof, e.g., allethrin, resmethrin, permethrin, tralomethrin), andnicotine, that is often employed as an acaricide. Other contemplatedcombinations are with miscellaneous pesticides including: bacillusthuringensis, chlorobenzilate, formamidines (e.g., amitraz), coppercompounds (e.g., copper hydroxide and cupric oxychloride sulfate),cyfluthrin, cypermethrin, dicofol, endosulfan, esenfenvalerate,fenvalerate, lambda-cyhalothrin, methoxychlor and sulfur.

Of note are additional biologically active compounds or agents selectedfrom art-known anthelmintics, such as, for example, avermectins (e.g.,ivermectin, moxidectin, milbemycin), benzimidazoles (e.g., albendazole,triclabendazole), salicylanilides (e.g., closantel, oxyclozanide),substituted phenols (e.g., nitroxynil), pyrimidines (e.g., pyrantel),imidazothiazoles (e.g., levamisole) and praziquantel.

Other biologically active compounds or agents useful in the compositionsof the present invention can be selected from Insect Growth Regulators(IGRs) and Juvenile Hormone Analogues (JHAs) such as diflubenzuron,triflumuron, fluazuron, cyromazine, methoprene, etc., thereby providingboth initial and sustained control of parasites (at all stages of insectdevelopment, including eggs) on the animal subject, as well as withinthe environment of the animal subject.

Of note are biologically active compounds or agents useful in thecompositions of the present invention selected from the antiparasiticclass of avermectin compounds. As stated above, the avermectin family ofcompounds is a series of very potent antiparasitic agents known to beuseful against a broad spectrum of endoparasites and ectoparasites inmammals.

A notable compound for use within the scope of the present invention isivermectin. Ivermectin is a semi-synthetic derivative of avermectin andis generally produced as a mixture of at least 80%22,23-dihydroavermectin B_(1a) and less than 20% 22,23-dihydroavermectinB_(1b). Ivermectin is disclosed in U.S. Pat. No. 4,199,569.

Abamectin is an avermectin that is disclosed as Avermectin B_(1a)/B_(1b)in U.S. Pat. No. 4,310,519. Abamectin contains at least 80% ofavermectin B_(1a) and not more than 20% of avermectin B_(1b).

Another notable avermectin is Doramectin, also known as25-cyclohexyl-avermectin B₁. The structure and preparation of Doramectinis disclosed in U.S. Pat. No. 5,089,480.

Another notable avermectin is Moxidectin. Moxidectin, also known asLL-F28249 alpha, is known from U.S. Pat. No. 4,916,154.

Another notable avermectin is Selamectin. Selamectin is25-cyclohexyl-25-de(1-methylpropyl)-5-deoxy-22,23-dihydro-5-(hydroxyimino)-avermectinB₁ monosaccharide.

Milbemycin, or B41, is a substance which is isolated from thefermentation broth of a Milbemycin producing strain of Streptomyces. Themicroorganism, the fermentation conditions and the isolation proceduresare more fully described in U.S. Pat. No. 3,950,360 and U.S. Pat. No.3,984,564.

Emamectin (4″-deoxy-4″-epi-methylaminoavermectin B₁), which can beprepared as described in U.S. Pat. No. 5,288,710 or U.S. Pat. No.5,399,717, is a mixture of two homologues,4″-deoxy-4″-epi-methylaminoavermectin B_(1a) and4″-deoxy-4″-epi-methylaminoavermectin B_(1b). Preferably, a salt ofEmamectin is used. Non-limiting examples of salts of Emamectin which canbe used in the present invention include the salts described in U.S.Pat. No. 5,288,710, e.g., salts derived from benzoic acid, substitutedbenzoic acid, benzenesulfonic acid, citric acid, phosphoric acid,tartaric acid, maleic acid, and the like. Most preferably, the Emamectinsalt used in the present invention is Emamectin benzoate.

Eprinomectin is chemically known as4″-epi-acetylamino-4″-deoxy-avermectin B₁. Eprinomectin was specificallydeveloped to be used in all cattle classes and age groups. It was thefirst avermectin to show broad-spectrum activity against both endo- andectoparasites while also leaving minimal residues in meat and milk. Ithas the additional advantage of being highly potent when deliveredtopically.

The composition of the present invention optionally comprisescombinations of one or more of the following antiparasite compounds:imidazo[1,2-b]pyridazine compounds as described by U.S. application Ser.No. 11/019,597, filed on Dec. 22, 2004, and published on Aug. 18, 2005as US 2005-0182059A1; 1-(4-mono anddi-halomethylsulphonylphenyl)-2-acylamino-3-fluoropropanol compounds, asdescribed by U.S. application Ser. No. 11/018,156, filed on Dec. 21,2004, now U.S. Pat. No. 7,361,689; trifluoromethanesulfonanilide oximeether derivatives, as described by U.S. application Ser. No. 11/231,423,filed on Sep. 21, 2005, now U.S. Pat. No. 7,312,248; andn-[(phenyloxy)phenyl]-1,1,1-trifluoromethanesulfonamide andn-[(phenylsulfanyl)phenyl]-1,1,1-trifluoromethanesulfonamidederivatives, as described by U.S. Provisional Application Ser. No.60/688,898, filed on Jun. 9, 2005, and published as US 2006-0281695A1 onDec. 14, 2006.

The compositions of the present invention can also further comprise aflukicide. Suitable flukicides include, for example, triclabendazole,fenbendazole, albendazole, Clorsulon and oxibendazole. It will beappreciated that the above combinations can further include combinationsof antibiotic, antiparasitic and anti-fluke active compounds.

In addition to the above combinations, it is also contemplated toprovide combinations of the inventive methods and compounds, asdescribed herein, with other animal health remedies such as traceelements, anti-inflammatories, anti-infectives, hormones, dermatologicalpreparations, including antiseptics and disinfectants, andimmunobiologicals such as vaccines and antisera for the prevention ofdisease.

For example, such antinfectives include one or more antibiotics that areoptionally co-administered during treatment using the inventivecompounds or methods, e.g., in a combined composition and/or in separatedosage forms. Art-known antibiotics suitable for this purpose include,for example, those listed herein below.

One useful antibiotic is Florfenicol, also known asD-(threo)-1-(4-methylsulfonylphenyl)-2-dichloroacetamido-3-fluoro-1-propanol.Another notable antibiotic compound isD-(threo)-1-(4-methylsulfonyphenyl)-2-difluoroacetamido-3-fluoro-1-propanol.Another useful antibiotic is Thiamphenicol. Processes for themanufacture of these antibiotic compounds, and intermediates useful insuch processes, are described in U.S. Pat. No. 4,311,857; U.S. Pat. No.4,582,918; U.S. Pat. No. 4,973,750; U.S. Pat. No. 4,876,352; U.S. Pat.No. 5,227,494; U.S. Pat. No. 4,743,700; U.S. Pat. No. 5,567,844; U.S.Pat. No. 5,105,009; U.S. Pat. No. 5,382,673; U.S. Pat. No. 5,352,832;and U.S. Pat. No. 5,663,361. Other florfenicol analogs and/or prodrugshave been disclosed and such analogs also can be used in thecompositions and methods of the present invention (see e.g., U.S. PatentApplication Publication No: 2004/0082553, now U.S. Pat. No. 7,041,670,and U.S. patent application Ser. No. 11/016,794, now U.S. Pat. No.7,153,842).

Another useful antibiotic compound is Tilmicosin. Tilmicosin is amacrolide antibiotic that is chemically defined as20-dihydro-20-deoxy-20-(cis-3,5-dimethylpiperidin-1-yl)-desmycosin andwhich is reportedly disclosed in U.S. Pat. No. 4,820,695.

Another useful antibiotic for use in the present invention istulathromycin. Tulathromycin is also identified as(2R,3S,4R,5R,8R,100R,11R,12S,13S,14R)13-[(2,6-dideoxy-3-C-methyl-3-O-methyl-4-C-[(propylamino)methyl]-alpha-L-ribo-hexopyranosyl]-oxy]-2-ethyl-3,4,10-trihydroxy-3,5,8,10,12,14-hexamethyl-11-[[3,4,6-trideoxy-3-(dimethyl-amino)-beta-D-xylo-hexopyranosyl]oxy]-1-oxa-6-azacyclopentadecan-15-one.Tulathromycin can be prepared in accordance with the procedures setforth in U.S. Patent Publication No. 2003/0064939 A1.

Further antibiotics for use in the present invention include thecephalosporins such as, for example, ceftiofur, cefquinome, etc. Theconcentration of the cephalosporin in the formulation of the presentinvention optionally varies between about 1 mg/mL to 500 mg/mL.

Another useful antibiotic includes the fluoroquinolones, such as, forexample, enrofloxacin, danofloxacin, difloxacin, orbifloxacin andmarbofloxacin. Enrofloxacin is typically administered in a concentrationof about 100 mg/mL. Danofloxacin is typically administered at aconcentration of about 180 mg/mL.

Other useful macrolide antibiotics include compounds from the class ofketolides, or, more specifically, the azalides. Such compounds aredescribed in, for example, U.S. Pat. No. 6,514,945, U.S. Pat. No.6,472,371, U.S. Pat. No. 6,270,768, U.S. Pat. No. 6,437,151, U.S. Pat.No. 6,271,255, U.S. Pat. No. 6,239,112, U.S. Pat. No. 5,958,888, U.S.Pat. No. 6,339,063 and U.S. Pat. No. 6,054,434.

Other useful antibiotics include the tetracyclines, particularlychlortetracycline and oxytetracycline. Other antibiotics may include3-lactams such as penicillins, e.g., penicillin, ampicillin,amoxicillin, or a combination of amoxicillin with clavulanic acid orother beta lactamase inhibitors.

Nonagronomic applications in the veterinary sector are by conventionalmeans such as by enteral administration in the form of, for example,tablets, capsules, drinks, drenching preparations, granulates, pastes,boli, feed-through procedures, or suppositories; or by parenteraladministration, such as by injection (including intramuscular,subcutaneous, intravenous, intraperitoneal) or implants; by nasaladministration; by topical administration, for example, in the form ofimmersion or dipping, spraying, washing, coating with powder, orapplication to a small area of the animal, and through articles such asneck collars, ear tags, tail bands, limb bands or halters which comprisecompounds or compositions of the present invention.

Any of the compounds of the present invention, or a suitable combinationof such compounds, may be administered directly to the animal subjectand/or indirectly by applying it to the local environment in which theanimal dwells (such as bedding, enclosures, or the like). Directadministration includes contacting the skin, fur or feathers of asubject animal with the compounds, or by feeding or injecting thecompounds into the animal.

The compounds of the present invention may be administered in acontrolled release form, e.g., in a subcutaneous slow releaseformulation, or in the form of a controlled release device affixed to ananimal such as a fleacollar. Collars for the controlled release of aninsecticide agent for long term protection against flea infestation in acompanion animal are art-known, and are described, for example, by U.S.Pat. No. 3,852,416, U.S. Pat. No. 4,224,901, U.S. Pat. No. 5,555,848 andU.S. Pat. No. 5,184,573.

Typically a parasiticidal composition according to the present inventioncomprises a mixture of a compound of Formula 1, an N-oxide, or saltthereof, with one or more pharmaceutically or veterinarily acceptablecarriers comprising excipients and auxiliaries selected with regard tothe intended route of administration (e.g., oral, topical or parenteraladministration such as injection) and in accordance with standardpractice. In addition, a suitable carrier is selected on the basis ofcompatibility with the one or more active ingredients in thecomposition, including such considerations as stability relative to pHand moisture content. Therefore of note is a composition for protectingan animal from an invertebrate parasitic pest comprising a parasiticallyeffective amount of a compound of the invention and at least onecarrier.

For parenteral administration including intravenous, intramuscular andsubcutaneous injection, a compound of the present invention can beformulated in suspension, solution or emulsion in oily or aqueousvehicles, and may contain adjuncts such as suspending, stabilizingand/or dispersing agents. The compounds of the present invention mayalso be formulated for bolus injection or continuous infusion.Pharmaceutical compositions for injection include aqueous solutions ofwater-soluble forms of active ingredients (e.g., a salt of an activecompound), preferably in physiologically compatible buffers containingother excipients or auxiliaries as are known in the art ofpharmaceutical formulation. Additionally, suspensions of the activecompounds may be prepared in a lipophilic vehicle. Suitable lipophilicvehicles include fatty oils such as sesame oil, synthetic fatty acidesters such as ethyl oleate and triglycerides, or materials such asliposomes. Aqueous injection suspensions may contain substances thatincrease the viscosity of the suspension, such as sodium carboxymethylcellulose, sorbitol, or dextran. Formulations for injection may bepresented in unit dosage form, e.g., in ampoules or in multi-dosecontainers. Alternatively, the active ingredient may be in powder formfor constitution with a suitable vehicle, e.g., sterile, pyrogen-freewater, before use.

In addition to the formulations described supra, the compounds of thepresent invention may also be formulated as a depot preparation. Suchlong acting formulations may be administered by implantation (forexample, subcutaneously or intramuscularly) or by intramuscular orsubcutaneous injection. The compounds of the present invention may beformulated for this route of administration with suitable polymeric orhydrophobic materials (for instance, in an emulsion with apharmacologically acceptable oil), with ion exchange resins, or as asparingly soluble derivative such as, without limitation, a sparinglysoluble salt.

For administration by inhalation, the compounds of the present inventioncan be delivered in the form of an aerosol spray using a pressurizedpack or a nebulizer and a suitable propellant, e.g., without limitation,dichlorodifluoromethane, trichlorofluoromethane,dichlorotetrafluoroethane or carbon dioxide. In the case of apressurized aerosol, the dosage unit may be controlled by providing avalve to deliver a metered amount. Capsules and cartridges of, forexample, gelatin for use in an inhaler or insufflator may be formulatedcontaining a powder mix of the compound and a suitable powder base suchas lactose or starch.

Compounds of the present invention have been discovered to havefavorable pharmacokinetic and pharmacodynamic properties providingsystemic availability from oral administration and ingestion. Thereforeafter ingestion by the animal to be protected, parasiticidally effectiveconcentrations of compounds of the invention in the bloodstream protectthe treated animal from blood-sucking pests such as fleas, ticks andlice. Therefore of note is a composition for protecting an animal froman invertebrate parasite pest in a form for oral administration (i.e.comprising, in addition to a parasiticidally effective amount of acompound of the invention, one or more carriers selected from bindersand fillers suitable for oral administration and feed concentratecarriers).

For oral administration in the form of solutions (the most readilyavailable form for absorption), emulsions, suspensions, pastes, gels,capsules, tablets, boluses, powders, granules, rumen-retention andfeed/water/lick blocks, a compound of the present invention can beformulated with binders/fillers known in the art to be suitable for oraladministration compositions, such as sugars and sugar derivatives (e.g.,lactose, sucrose, mannitol, sorbitol), starch (e.g., maize starch, wheatstarch, rice starch, potato starch), cellulose and derivatives (e.g.,methylcellulose, carboxymethylcellulose, ethylhydroxycellulose), proteinderivatives (e.g., zein, gelatin), and synthetic polymers (e.g.,polyvinyl alcohol, polyvinylpyrrolidone). If desired, lubricants (e.g.,magnesium stearate), disintegrating agents (e.g., cross-linkedpolyvinylpyrrolidinone, agar, alginic acid) and dyes or pigments can beadded. Pastes and gels often also contain adhesives (e.g., acacia,alginic acid, bentonite, cellulose, xanthan gum, colloidal magnesiumaluminum silicate) to aid in keeping the composition in contact with theoral cavity and not being easily ejected.

If the parasiticidal compositions are in the form of feed concentrates,the carrier is typically selected from high-performance feed, feedcereals or protein concentrates. Such feed concentrate-containingcompositions can, in addition to the parasiticidal active ingredients,comprise additives promoting animal health or growth, improving qualityof meat from animals for slaughter or otherwise useful to animalhusbandry. These additives can include, for example, vitamins,antibiotics, chemotherapeutics, bacteriostats, fungistats, coccidiostatsand hormones.

The compounds of Formula 1 may also be formulated in rectal compositionssuch as suppositories or retention enemas, using, e.g., conventionalsuppository bases such as cocoa butter or other glycerides.

Formulations for topical administration are typically in the form of apowder, cream, suspension, spray, emulsion, foam, paste, aerosol,ointment, salve or gel. More typically a topical formulation is awater-soluble solution, which can be in the form of a concentrate thatis diluted before use. Parasiticidal compositions suitable for topicaladministration typically comprise a compound of the present inventionand one or more topically suitable carriers. In applications of aparasiticidal composition topically to the exterior of an animal as aline or spot (i.e. “spot-on” treatment), the active ingredient migratesover the surface of the animal to cover most or all of its externalsurface area. As a result, the treated animal is particularly protectedfrom invertebrate pests that feed off the epidermis of the animal suchas ticks, fleas and lice. Therefore formulations for topical localizedadministration often comprise at least one organic solvent to facilitatetransport of the active ingredient over the skin and/or penetration intothe epidermis of the animal. Carriers in such formulations includepropylene glycol, paraffins, aromatics, esters such as isopropylmyristate, glycol ethers, alcohols such as ethanol, n-propanol, 2-octyldodecanol or oleyl alcohol; solutions in esters of monocarboxylic acids,such as isopropyl myristate, isopropyl palmitate, lauric acid oxalicester, oleic acid oleyl ester, oleic acid decyl ester, hexyl laurate,oleyl oleate, decyl oleate, caproic acid esters of saturated fattyalcohols of chain length C₁₂-C₁₈; solutions of esters of dicarboxylicacids, such as dibutyl phthalate, diisopropyl isophthalate, adipic aciddiisopropyl ester, di-n-butyl adipate or solutions of esters ofaliphatic acids, e.g., glycols. It may be advantageous for acrystallization inhibitor or a dispersant known from the pharmaceuticalor cosmetic industry also to be present.

A pour-on formulation may also be prepared for control of parasites inan animal of agricultural worth. The pour-on formulations of thisinvention can be in the form of a liquid, powder, emulsion, foam, paste,aerosol, ointment, salve or gel. Typically, the pour-on formulation isliquid. These pour-on formulations can be effectively applied to sheep,cattle, goats, other ruminants, camelids, pigs and horses. The pour-onformulation is typically applied by pouring in one or several lines orin a spot-on the dorsal midline (back) or shoulder of an animal. Moretypically, the formulation is applied by pouring it along the back ofthe animal, following the spine. The formulation can also be applied tothe animal by other conventional methods, including wiping animpregnated material over at least a small area of the animal, orapplying it using a commercially available applicator, by means of asyringe, by spraying or by using a spray race. The pour-on formulationsinclude a carrier and can also include one or more additionalingredients. Examples of suitable additional ingredients are stabilizerssuch as antioxidants, spreading agents, preservatives, adhesionpromoters, active solubilisers such as oleic acid, viscosity modifiers,UV blockers or absorbers, and colourants. Surface active agents,including anionic, cationic, non-ionic and ampholytic surface activeagents, can also be included in these formulations.

The formulations of this invention typically include an antioxidant,such as BHT (butylated hydroxytoluene). The antioxidant is generallypresent in amounts of at 0.1-5% (wt/vol). Some of the formulationsrequire a solubilizer, such as oleic acid, to dissolve the active agent,particularly if spinosad is used. Common spreading agents used in thesepour-on formulations are: IPM, IPP, caprylic/capric acid esters ofsaturated C₁₂-C₁₈ fatty alcohols, oleic acid, oleyl ester, ethyl oleate,triglycerides, silicone oils and DPM. The pour-on formulations of thisinvention are prepared according to known techniques. Where the pour-onis a solution, the parasiticide/insecticide is mixed with the carrier orvehicle, using heat and stirring where required. Auxiliary or additionalingredients can be added to the mixture of active agent and carrier, orthey can be mixed with the active agent prior to the addition of thecarrier. If the pour-on is an emulsion or suspension, these formulationsare similarly prepared using known techniques.

Other delivery systems for relatively hydrophobic pharmaceuticalcompounds may be employed. Liposomes and emulsions are well-knownexamples of delivery vehicles or carriers for hydrophobic drugs. Inaddition, organic solvents such as dimethylsulfoxide may be used, ifneeded.

For agronomic applications, the rate of application required foreffective control (i.e. “biologically effective amount”) will depend onsuch factors as the species of invertebrate to be controlled, the pest'slife cycle, life stage, its size, location, time of year, host crop oranimal, feeding behavior, mating behavior, ambient moisture,temperature, and the like. Under normal circumstances, application ratesof about 0.01 to 2 kg of active ingredients per hectare are sufficientto control pests in agronomic ecosystems, but as little as 0.0001kg/hectare may be sufficient or as much as 8 kg/hectare may be required.For nonagronomic applications, effective use rates will range from about1.0 to 50 mg/square meter but as little as 0.1 mg/square meter may besufficient or as much as 150 mg/square meter may be required. Oneskilled in the art can easily determine the biologically effectiveamount necessary for the desired level of invertebrate pest control.

In general for veterinary use, a compound of Formula 1, an N-oxide, orsalt thereof, is administered in a parasiticidally effective amount toan animal to be protected from invertebrate parasite pests. Aparasiticidally effective amount is the amount of active ingredientneeded to achieve an observable effect diminishing the occurrence oractivity of the target invertebrate parasite pest. One skilled in theart will appreciate that the parasitically effective dose can vary forthe various compounds and compositions of the present invention, thedesired parasitical effect and duration, the target invertebrate pestspecies, the animal to be protected, the mode of application and thelike, and the amount needed to achieve a particular result can bedetermined through simple experimentation.

For oral administration to homeothermic animals, the daily dosage of acompound of the present invention typically ranges from about 0.01 mg/kgto about 100 mg/kg, more typically from about 0.5 mg/kg to about 100mg/kg, of animal body weight. For topical (e.g., dermal) administration,dips and sprays typically contain from about 0.5 ppm to about 5000 ppm,more typically from about 1 ppm to about 3000 ppm, of a compound of thepresent invention.

Representative compounds of this invention prepared by the methodsdescribed herein are shown in Index Tables A-E. See Index Table F for ¹HNMR data. For mass spectral data (AP⁺ (M+1)), the numerical valuereported is the molecular weight of the parent molecular ion (M) formedby addition of H⁺ (molecular weight of 1) to the molecule to give a M+1peak observed by mass spectrometry using atmospheric pressure chemicalionization (AP⁺). The alternate molecular ion peaks (e.g., M+2 or M+4)that occur with compounds containing multiple halogens are not reported.The variable “R^(A)” in Index Tables A-C represents one or a combinationof substituents as listed in Index Tables A-C.

The following abbreviations are used in the Index Tables which follow:Cmpd means Compound, Me is methyl, Et is ethyl, i-Pr is isopropyl, n-Buis normal-butyl, t-Bu is tertiary-butyl, Ph is phenyl, CHO is formyl, Acis acetyl (i.e. C(O)CH₃) and SO₂Me is methyl sulfonyl.

Fragments X-1 through X-6 shown below are referred to in the IndexTables. The wavy line denotes the attachment point of the fragment tothe remainder of the molecule.

INDEX TABLE A

AP+ Cmpd R^(A) R^(B) R^(3a) R^(3b) R^(3c) R^(3d) (M + 1) 1 3-OCF₃ X-2 HH H Br 532 2 H Pr H CH₃ H H 295 3 H Pr H H CH₃ H 295 4 H Pr CH₃ H H H295 5 H Pr H cyano H H 306 6 H Pr Cl H H H 315 8 H Pr H H H Cl 315 9 HX-1 F H H H 382 10 4-F X-1 F H H H 400 11 3-OCF₃ X-1 F H H H 466 12 2-F,4-F X-1 F H H H 418 13 3-OCF₃ X-1 H F H F * 14 2-F, 4-F X-1 H F H F * 154-F X-1 H F H F * 16 H CH₂CF₃ H H H OH * 17 4-F CH₂CF₃ H H H OH 355 183-CF₃ X-2 H H H Br 516 19 3-Br X-2 H H H Br 558 20 3-Cl, 5-CF₃ X-2 H H HBr 550 21 2-F, 3-Cl, 5-CF₃ X-2 H H H Br 600 22 3-OCF₃ X-2 H H H cyano479 23 3-OCF₃ X-2 H H H Cl 488 24 3-OCF₃ X-2 H H OCH₃ H 484 25 3-OCF₃X-2 H OCH₃ H H 484 26 3-OCF₃ X-2 H H H CH₃ 468 27 3-OCF₃ X-2 H H Br H532 28 3-CF₃ X-2 H H Br H 516 29 3-CF₃ X-2 H H H CH₃ 452 30 2-F X-2 H HH CH₃ 402 31 2-F X-2 H H Br H 466 32 2-F X-2 H H OCH₃ H 418 33 3-Cl,5-OCF₃ X-2 H H H Br 566 34 H X-2 H H CH₃ H 384 35 H X-2 H H Cl H 404 543-OCF₃ X-2 CH₃ H H H 468 55 2-F X-2 CH₃ H H H 402 61 3-OCF₃ X-2 H Br HCH₃ 546 63 2-F, 3-CF₃ X-2 H Br H CH₃ 470 430 2-F X-2 H I H H 514 * SeeIndex Table F for ¹H NMR data.

INDEX TABLE B

AP+ Cmpd R^(A) R^(B) R^(3d) m.p. (° C.) (M + 1) 36 3-Cl, 5-OCF₃ X-2 CH₃502 37 2-F, 6-F X-2 CH₃ 420 38 2-F X-1 CH₃ 396 39 3-OCF₃ X-1 CH₃ 462 403-SCF₃ X-2 CH₃ 484 41 2-F X-2 OCH₃ 418 42 H X-3 CH₃ * 43 3-OCF₃ X-3CH₃ * 44 2-F X-3 CH₃ * 45 3-CF₃ X-3 CH₃ * 46 2-F, 6-F X-3 CH₃ * 47 H X-2CH₃ 383 48 2-OCH₃, 5-OCH₃ X-2 CH₃ 443 49 2-F, 5-CF₃ X-2 CH₃ 470 50 4-FX-2 CH₃ 402 51 3-OCF₃ X-2 OCH₃ 484 52 2-F, 5-CF₃ X-2 OCH₃ 486 532-OCH₃,5-OCF₃ X-2 CH₃ 498 56 2-OCH₃ X-2 CII₃ 414 57 2-F,3-Cl,5-CF₃ X-2CH₃ 504 58 4-SCF₃ X-2 CH₃ 484 59 2-F, 4-F X-2 CH₃ 420 60 2-F, 3-Cl X-2CH₃ 436 62 3-OCH₃ X-2 CH₃ 414 64 3-SCF₃ X-4 CH₃ 462 65 3-I X-2 CH₃ 51066 2-F, 3-CF₃ X-2 OCH₃ 486 67 3-I X-2 CH₃ 476 68 3-OCF₃ X-2 Ph 530 693-OCH₃ X-2 Ph 476 70 3-OCF₃ X-5 CH₃ 434 71 3-OCF₃ X-6 CH₃ 448 72 3-OCF₃X-4 CH₃ 446 73 3-CF₃ X-5 CH₃ 418 74 3-CF₃ X-6 CH₃ 432 75 3-CF₃ X-4 CH₃430 76 2-F X-5 CH₃ 368 77 2-F X-6 CH₃ 382 78 2-F X-4 CH₃ 380 79 3-Br,5-CF₃ X-2 CH₃ 530 80 3-Br, 5-OCF₃ X-2 CH₃ 546 81 3-Cl, 5-CF₃ X-2 CH₃ 48682 3-F, 5-CF₃ X-2 CH₃ 470 83 3-I, 5-OCH₃ X-2 CH₃ 540 84 3-Br X-2 CH₃ 462101 3-(C≡CH) X-2 CH₃ 408 102 3-(CH═CH₂) X-2 CH₃ 410 103 2-Cl, 5-CF₃ X-2CH₃ 486 104 2-F, 3-OCH₃ X-2 CH₃ 432 105 4-Cl X-2 CH₃ 418 1063,4-(-OCH₂O—) X-2 CH₃ 428 107 3-CF₃ CH₂CF₃ CH₃ 403 108 2-OCH₃, 3-F, 5-FX-2 CH₃ 450 109 2-OCH₃, 3-OCH₃, X-2 CH₃ 444 110 3-F, 4-F, 5-F X-2 CH₃438 111 2-F, 4-OCH₃ X-2 CH₃ 432 112 3-OCH₃, 4-F X-2 CH₃ 432 113 3-Cl,5-Cl X-2 CH₃ 452 114 3-OCH₃, 4-OCH₃ X-2 CH₃ 444 115 4-OCH₃ X-2 CH₃ 414116 2-OCH₃, 4-OCH₃ X-2 CH₃ 444 117 3-F, 4-OCH₃ X-2 CH₃ 432 118 3-Cl X-2CH₃ 418 119 3-F, 4-F X-2 CH₃ 420 120 3-CF₃, 4-F X-2 CH₃ 470 121 2-OCH₃,5-CF₃ X-2 CH₃ 482 122 3-CH₃ X-2 CH₃ 398 123 3-CH₂CH₃ X-2 CH₃ 412 1242-OCH₃, 5-F X-2 CH₃ 432 125 2-F, 3-F X-2 CH₃ 420 126 2-OCH₃, 5-Br X-2CH₃ 492 127 2-F, 5-Cl X-2 CH₃ 436 128 3-OCF₃, 4-Cl X-2 CH₃ 502 1292-OCH₃, 5-Cl X-2 CH₃ 448 130 2-Cl, 5-Cl X-2 CH₃ 452 131 3-Cl, 5-CF₃ X-2OCH₃ 502 132 3-OCH₃, 5-OCH₃ X-2 CH₃ 444 133 3-Cl, 5-CF₃ X-6 CH₃ 466 1342-Cl, 3-Cl X-2 CH₃ 452 135 3-OCH₂CH₃ X-2 CH₃ 428 136 3-OCF₃ X-2 CH₂CH₃482 152 2-OCH₂CH₃ X-2 CH₃ 428 153 H X-2 CH═CH₂ 396 154 3-CF₃ X-2 CH═CH₂464 155 2-F X-2 CH═CH₂ 414 156 3-CF₃ CH₂(1-methyl-4- CH₃ 415 imidazolyl)157 2-F, 5-Br X-2 CH₃ 480 158 3-F, 4-Cl X-2 CH₃ 436 159 3-F X-2 CH₃ 402160 3,5-diF X-2 CH₃ 420 161 2-F, 4-Cl X-2 CH₃ 436 162 3,4-diCl X-2 CH₃452 163 3-Br, 5-F X-2 CH₃ 480 164 3-CH₃, 4-Cl X-2 CH₃ 432 165 2,5-diFX-2 CH₃ 420 166 2-Cl, 4-F X-2 CH₃ 436 167 3-CH₃, 5-CF₃ X-2 CH₃ 466 1683-CH₃, 5-Cl X-2 CH₃ 462 169 2-CH₃, 4-Br X-2 CH₃ 476 170 3-Br, 4-F X-2CH₃ 480 173 3-OCF₃, 4-F X-2 CH₃ 486 179 2-F X-2 CH₂CH₃ 416 1803-OCH₂CH₃, 5-OCH₂CH₃ X-2 CH₃ 440 181 2-CH₃, 5-Cl X-2 CH₃ 432 182 2-OCH₃,5-CH₃ X-2 CH₃ 428 183 2-F, 5-CH₃ X-2 CH₃ 416 185 H X-2 Cl 404 186 2-FX-2 Cl 421 187 3-C(CH₃)₃ X-2 CH₃ 440 188 3-Cl, 5-CF₃ X-2 CH₂CH₃ 500 1923-(4-chlorophenyl) X-2 CH₂CH₃ 508 196 2-F, 3-CH₃ X-2 CH₃ 416 197 2-OCH₃,3-CH₃ X-2 CH₃ 428 198 3-Br X-2 CH₂CH₃ 476 202 3-(4-chlorophenyl) X-2OCH₃ 510 203 3-CH₂CH₂CH₃ X-2 CH₃ 426 204 2-CH₃ X-2 CH₃ 398 205 4-CH₃ X-2CH₃ 398 206 2-Cl X-2 CH₃ * 212 2-F X-2 I 514 213 2-F X-2 CH₂F 420 216 HX-2 CH₂F 402 217 3-CF₃ X-2 CH₂F 470 218 H X-2 I * 223 4-F X-2 OCH₃ 418224 2-nitro X-2 CH₃ * 225 2-nitro, 5-CF₃ X-2 CH₃ * 226 H X-2CH₂OC(O)CH₃ * 227 3-CH₃, 5-CH₃ X-2 CH₃ 411 228 3-Cl, 4-F X-2 CH₃ 436 2343-cyano, 4-F X-2 CH₃ 428 235 3-Br, 5-CH₃ X-2 CH₃ 476 236 4-cyano X-2 CH₃409 237 4-nitro X-2 CH₃ * 240 3-cyano, 5-CF₃ X-2 CH₃ 477 241 3-CH(CH₃)₂X-2 CH₃ 426 243 3-Si(CH₂CH₃)₃ X-2 CH₃ 498 244 3-Si(CH₃)₃ X-2 CH₃ 456 2493-OSi(CH(CH₃)₂)₃ X-2 CH₃ 556 257 3-Br, 5-Cl X-2 CH₃ 496 265 3-CH₃,5-Si(CH₃)₃ X-2 CH₃ 470 266 3-OCH₃, 5-C(O)OCH₃ X-2 CH₃ 472 268 3-cyano,5-OCH₃ X-2 CH₃ 539 296 3-Br, 5-cyano X-2 CH₃ 487 297 3-F, 5-cyano X-2CH₃ 427 298 3-Cl, 5-cyano X-2 CH₃ 443 304 3-cyano, 5-CH₃ X-2 CH₃ 423 3102-I X-2 CH₃ 510 311 3-cyano X-2 CH₃ 409 312 2-cyano X-2 CH₃ 409 324 2-F,5-cyano X-2 CH₃ 427 335 3,5-diCl, 4-F X-2 CH₃ * 339 3-C(O)OCH₃ X-2 CH₃442 342 2-Cl, 5-Br X-2 CH₃ 496 348 H 2-methyl-1- CH₃ * imidazolyl 349 H4-methyl-1- CH₃ * imidazolyl 350 H 2,4-dimethyl-1- CH₃ 361 imidazolyl351 3-Cl, 5-C(O)OCH₃ X-2 CH₃ 476 353 3-Br, 4-CH₃ X-2 CH₃ 475 3543-(2-chloro-4-(trifluoromethyl)phenyl) X-2 OCH₃ 578 3553-(2-fluoro-4-(trifluoromethyl)phenyl) X-2 OCH₃ 562 370 H 1-imidazolyl333 373 3-C(O)CH₃ X-2 CH₃ 426 380 3-CF₃, 5-C(O)OCH₃ X-2 CH₃ 510 3823-cyclopropyl X-2 CH₃ 424 389 3,5-diCl CH₂CH₂CH₂OCH₃ CH₃ 393 390 HCH₂CH₂CH₂OCH₃ CH₃ 107-109 392 2-F CH₂CH₂CH₂OCH₃ 109-110 395 3-Cl, 5-FX-2 CH₃ 436 396 4-C(O)OCH₃ X-2 CH₃ 442 397 4-C(O)CH₃ X-2 CH₃ 426 4033-F, 5-CF₃ X-2 OCH₃ 486 404 3-Cl, 5-OCH₃ X-2 CH₃ 448 405 3-CH₃, 4-F X-2CH₃ 416 406 H 3-methyl-5- CH₃ 109-111 isoxazolyl 4134-(2-chloro-4-(trifluoromethyl)phenyl) X-2 CH₃ 562 414 4-I X-2 CH₃ 510415 4-(2-chloro-4-fluorophenyl) X-2 CH₃ 512 4164-(3-chloro-5-(trifluoromethyl)phenyl) X-2 CH₃ 562 417 2-F CH₂(3- CH₃354 tetrahydrofuranyl) 420 4-(3-chloro-4-(trifluoromethyl)phenyl) X-2CH₃ 564 423 2-(2-chloro-4-(trifluoromethyl)phenyl) X-2 CH₃ 562 424 3-F,5-OCH₃ X-2 CH₃ 432 425 3-Cl, 5-I X-2 CH₃ 544 426 3-OCH₃, 5-CF₃ X-2 CH₃482 428 2-(2-chloro-4-fluorophenyl) X-2 CH₃ 512 436 H CH₂(3- CH₃ 208-211tetrahydrofuranyl) 439 3-(C(CH₃)═NOCH₃) X-2 CH₃ 455 442 3-Cl, 5-F X-2OCH₃ 452 445 3-(2-chloro-4-(trifluoromethyl)phenyl) CH₂CH₂CH₂OCH₃ CH₃144-146 446 3,5-diCl CH₂(3- CH₃ >300 tetrahydrofuranyl) 452 2-OCH₃, 5-CNX-2 CH₃ 439 453 3-(C(CH₃)═NOCH₂CH₃) X-2 CH₃ 469 458 3-thienyl X-2 CH₃466 459 3-OCF₃ CH₂(3- CH₃ 420 tetrahydrofuranyl) 460 3-OCF₃CH₂CH₂CH₂OCH₃ CH₃ 408 463 3-(2,4-dimethylphenyl) X-2 CH₃ 504 469 2-FCH₂(3-methyl-5- CH₃ 162-164 isoxazolyl) 4703-(2-chloro-4-(trifluoromethyl)phenyl) CH₂(3-methyl-5- CH₃ 181-182isoxazolyl) 471 3,5-diCl CH₂(3-methyl-5- CH₃ 184-186 isoxazolyl) 472 HCH₂CF₃ CH₃ 138-140 473 2-F CH₂CF₃ CH₃ 188-190 475 H CH₂(5-thiazolyl) CH₃174-176 476 3,5-diCl CH₂(5-thiazolyl) CH₃ 200-201 4773-(2-chloro-4-(trifluoromethyl)phenyl) CH₂(5-thiazolyl) CH₃ 107-109 478H CH₂(2-methyl-5- CH₃ 164-166 thiazolyl) 4793-(2-chloro-4-(trifluoromethyl)phenyl) CH₂(2-methyl-5- CH₃ 199-200thiazolyl) 480 3-(2-chloro-4- X-2 OCH₃ 596 (trifluoromethyl)phenyl), 4-F481 3-Cl, 5-(4-chloro-2-fluorophenyl) X-2 OCH₃ 562 486 3-Cl, 4-Br X-2CH₃ 498 487 3-CF₃, 4-Br X-2 CH₃ 531 488 2-F, 3-Cl, 4-Br X-2 CH₃ * 494 HCH₂(2-chloro-4- CH₃ 452 (trifluoromethyl)-5- thiazolyl) 495 3-CH₃,5-OCH₃ X-2 CH₃ 429 496 3-F, 5-I X-2 CH₃ 528 497 3-CH₃, 5-I X-2 CH₃ 524498 3-CH₃, 5-F X-2 CH₃ 416 * See Index Table F for ¹H NMR data.

INDEX TABLE C

m.p. AP+ Cmpd R^(A) R (° C.) (M + 1) 85 H 3-(trifluoromethoxy)phenyl 54486 H 2,5-difluorophenyl 496 87 5-OCF₃ 6-chloro-3-pyridinyl 579 88 H2,3-dichlorophenyl 528 89 H 2,4-dichlorophenyl 528 90 H5-cyano-2-ethoxyphenyl 515 137 H 4-(trifluoromethyl)phenyl 528 138 H5-chloro-2-fluorophenyl 512 139 H 2,5-dichlorophenyl 528 140 H4-chlorophenyl 494 150 H 3 -chloro-4-(trifluoromethyl)phenyl 562 151 H2-chloro-5-fluorophenyl 512 174 5-OCH₃ 4-chlorophenyl 524 175 H—O-(4-fluorophenyl) 494 176 H —O-(2-fluorophenyl) 494 177 H—O-(3-fluorophenyl) 494 178 5-F 4-chlorophenyl 512 184 H —O-(phenyl) 476189 H 2-chloro-4-fluorophenyl 510 190 H 4-chloro-2-fluorophenyl 512 191H 2-chloro-4-(trifluoromethyl)phenyl 562 193 H 4-bromophenyl 538 194 H4-methylphenyl 474 195 H 4-fluorophenyl 478 199 H2-methyl-4-chlorophenyl 508 200 H 3-chlorophenyl 494 201 H3-chloro-4-fluorophenyl 512 207 H 4-chloro-3-fluorophenyl 512 208 4-F4-chlorophenyl 512 209 4-F 4-chloro-2-fluorophenyl 530 210 6-OCH₃4-chlorophenyl 523 211 6-OCH₃ 4-chloro-2-fluorophenyl 542 214 6-F4-chloro-2-fluorophenyl 530 215 6-F 4-chlorophenyl 512 219 H—O-(2,5-dichlorophenyl) 544 220 H —O-(4-chlorophenyl) 510 221 H—O-(4-methoxyphenyl) 506 222 H —O-(4-cyanophenyl) 501 229 H2-fluoro-4-(trifluoromethyl)phenyl 546 230 H 4-bromo-2-fluorophenyl 558231 H 2-fluoro-5-(trifluoromethoxy)phenyl 562 232 H4-chloro-2-methoxyphenyl 524 233 H 5-cyano-2-fluorophenyl 504 238 4-OCH₃4-chloro-2-fluorophenyl 542 239 4-OCH₃ 4-chlorophenyl 524 246 5-CH₃6-(trifluoromethyl)-3-pyridinyl 543 247 H 3-cyano-4-fluorophenyl 503 248H 2,4-difluorophenyl 496 250 6-OCH₃ 2-chloro-4-fluorophenyl 542 251 4-F2-chloro-4-fluorophenyl 530 252 H —O-(4-bromophenyl) 554 253 H—O-(2-chloro-4-fluorophenyl) 528 255 H 2-methylphenyl 474 256 5-Cl4-chlorophenyl 528 258 H —C(O)(4-chlorophenyl) 523 259 H—CH₂(4-chlorophenyl) 509 262 5-Cl 2,4-dichlorophenyl 562 263 5-F4-(trifluoromethyl)phenyl 546 264 5-Cl 4-(trifluoromethyl)phenyl 562 269H phenyl 460 270 6-F 4-fluorophenyl 496 271 H 3,5-difluorophenyl 496 272H 2-methyl-4-(trifluoromethyl)phenyl 542 273 5-Cl6-(trifluoromethyl)-3-pyridinyl 563 276 5-CF₃ 4-chloro-2-methylphenyl576 277 H 3-chloro-5-(trifluoromethyl)phenyl 564 278 4-CH₃2-chloro-4-(trifluoromethyl)phenyl 576 279 5-CF₃ 6-chloro-3-pyridinyl563 285 H 4-chloro-2-(trifluoromethyl)phenyl 567 286 5-CF₃4-chlorophenyl 567 287 H —S-(4-(trifluoromethyl)phenyl) 561 289 4-F2-chloro-4-(trifluoromethyl)phenyl 580 290 4-F6-(trifluoromethyl)-3-pyridinyl 547 291 4-F 2,4-dichlorophenyl 546 2996-F 6-(trifluoromethyl)-3-pyridinyl 547 300 6-F4-(trifluoromethyl)phenyl 546 301 6-Cl 4-(trifluoromethyl)phenyl 562 3026-Cl 6-(trifluoromethyl)-3-pyridinyl 563 305 4-Cl4-(trifluoromethyl)phenyl 562 306 4-Cl 6-(trifluoromethyl)-3-pyridinyl563 307 H 2,6-dichloro-3-pyridinyl 529 308 5-Cl 2,6-dichloro-3-pyridinyl563 315 H 4,6-dichlorophenyl-3-pyridinyl 531 316 4-CH₃4-(trifluoromethyl)phenyl 542 317 4-CH₃ 6-(trifluoromethyl)-3-pyridinyl543 318 6-CH₃ 6-(trifluoromethyl)-3-pyridinyl 543 319 6-CH₃2-chloro-4-(trifluoromethyl)phenyl 576 320 6-CH₃4-(trifluoromethyl)phenyl 542 321 4-OCH₃2-chloro-4-(trifluoromethyl)phenyl 592 322 6-OCH₃4-(trifluoromethyl)phenyl 558 323 6-OCH₃2-chloro-4-(trifluoromethyl)phenyl 592 325 H 4-cyanophenyl 485 326 H4-chloro-2-cyanophenyl 519 327 H 4-carbomethoxy-2-chlorophenyl 535 3286-Cl 2-methyl-4-(trifluoromethyl)phenyl 576 329 4-OCH₃4-(trifluoromethyl)phenyl 558 330 4-F 3-chloro-5-(trifluoromethyl)phenyl 580 336 4-OCH₃2-fluoro-4-(trifluoromethyl)phenyl 576 337 H 3-bromo-5-fluorophenyl 556338 4-CN 2-chloro-4-(trifluoromethyl)phenyl 587 343 6-F2-chloro-4-(trifluoromethyl)phenyl 580 344 4-Cl2-chloro-4-(trifluoromethyl)phenyl 596 345 4-OCH₃6-(trifluoromethyl)-3-pyridinyl 559 346 4-CH₃ 4-chloro-2-fluorophenyl526 347 H 3 -chloro-5-fluorophenyl 512 352 5-CH₃2-chloro-4-(trifluoromethyl)phenyl 576 362 H 4-(methylthio)phenyl 506363 4-F 2-fluoro-4-(trifluoromethyl)phenyl 564 364 4-F2-methyl-4-(trifluoromethyl)phenyl 560 365 4-F 4-chloro-2-methylphenyl526 366 H 2,4-dimethylphenyl 488 367 H2-chloro-5-(trifluoromethyl)phenyl 562 368 4-F4-chloro-2-(trifluoromethyl)phenyl 580 369 4-Cl 4-chloro-2-fluorophenyl546 374 4-F 2-fluoro-5-(trifluoromethoxy)phenyl 580 375 H2,4-bis(trifluoromethyl)phenyl 596 376 4-OCH₃4-chloro-2-(trifluoromethyl)phenyl 592 377 4-OCH₃2-methyl-4-(trifluoromethyl)phenyl 572 378 4-OCH₃4-chloro-2-methylphenyl 538 381 5-CH₃ 4-chloro-2-fluorophenyl 526 384 H6-chloro-2-fluoro-3-pyridinyl 513 385 4-CH₃2-chloro-4-(trifluoromethyl)phenyl 560 386 4-OCH₃4-chloro-3-fluorophenyl 542 387 4-F 4-chloro-3-fluorophenyl 530 388 4-F3 -chloro-4-(trifluoromethyl)phenyl 580 398 4-OCH₃2-fluoro-5-(trifluoromethoxy)phenyl 592 399 4-F 2,6-dichloro-3-pyridinyl547 400 H 3 -chloro-4-(trifluoromethyl)phenyl 562 401 5-Cl2-chloro-4-(trifluoromethyl)phenyl 596 402 5-Cl 4-chloro-2-fluorophenyl546 407 5-Cl 2-methyl-4-(trifluoromethyl)phenyl 576 408 5-Cl2-fluoro-5-(trifluoromethoxy)phenyl 596 409 4-CH₃2-fluoro-5-(trifluoromethoxy)phenyl 576 410 5-Cl2-fluoro-4-(trifluoromethyl)phenyl 580 411 4-CH₃4-chloro-2-(trifluoromethyl)phenyl 576 412 5-CF₃2-chloro-4-(trifluoromethyl)phenyl 630 421 6-F2-fluoro-4-(trifluoromethyl)phenyl 564 422 6-OCH₃2-fluoro-4-(trifluoromethyl)phenyl 576 427 4-F2-chloro-5-(trifluoromethyl)phenyl 580 429 4-CH₃2-chloro-5-(trifluoromethyl)phenyl 576 431 4-OCH₃2-chloro-5-(trifluoromethyl)phenyl 592 432 6-F2-methyl-4-(trifluoromethyl)phenyl 560 433 5-F2-chloro-4-(trifluoromethyl)phenyl 580 434 5-F2-chloro-5-(trifluoromethyl)phenyl 580 435 5-F2-methyl-4-(trifluoromethyl)phenyl 560 437 H 4-chloro-3-cyanophenyl 519438 H 4-cyano-2-fluorophenyl 503 440 4-CH₃2-methyl-4-(trifluoromethyl)phenyl 556 441 5-F 4-chloro-2-fluorophenyl530 443 4-F 2,4-bis(trifluoromethyl)phenyl 614 448 4-OCH₃2-fluoro-5-(trifluoromethyl)phenyl 576 449 H2-fluoro-5-(trifluoromethyl)phenyl 546 450 4-F2-fluoro-5-(trifluoromethyl)phenyl 564 451 5-OCH₃2-chloro-4-(trifluoromethyl)phenyl 592 457 H4-fluoro-2-(trifluoromethyl)phenyl 546 462 5-CN2-chloro-4-(trifluoromethyl)phenyl 587 464 H2-ethoxy-6-(trifluoromethyl)-3-pyridinyl 572 467 H2-chloro-6-(trifluoromethyl)-3-pyridinyl 563 468 5-Cl2-fluoro-5-(trifluoromethyl)phenyl 566 474 H2-chloro-4-(trifluoromethyl)phenyl 154- 155 482 4-Cl2-methyl-4-(trifluoromethyl)phenyl 576 483 4-CH₃2-fluoro-5-(trifluoromethyl)phenyl 560 484 4-CH₃2,4-bis(trifluoromethyl)phenyl 610 485 5-F2-fluoro-4-(trifluoromethyl)phenyl 564 489 4-OCH₃2,4-bis(trifluoromethyl)phenyl 676 490 5-OCH₃2-fluoro-4-(trifluoromethyl)phenyl 576 491 5-OCH₃4-chloro-2-fluorophenyl 542 493 5-CN 4-chloro-2-fluorophenyl 537 4995-Cl 4,6-dichloro-3-pyridinyl 563 500 5-F2-fluoro-5-(trifluoromethyl)phenyl 564 501 4-F4-fluoro-2-(trifluoromethyl)phenyl 564

INDEX TABLE D

AP+ Cmpd R^(A) m.p. (° C.) (M + 1) 242 SCF₃ * 245 CH₂CH₂CH₂CH₃ 364 2542-(4-(trifluoromethyl)phenyl)-4- 529 pyridinyl 2602-(4-chlorophenoxy)-4- * pyrimidinyl 261 2-bromo-4-pyridinyl 463 2672-(4-(trifluoromethyl)phenyl)-4- 530 pyrimidinyl 2742-chloro-6-(trifluoromethyl)-4- 486 pyridinyl 275 CH₃ * 280 CH(CH₃)₂ *281 CH₂C₆H₅ * 282 CH₂CH₃ * 283 CH(CH₃)CH₂CH₂CH₃ 378 284 C(CH₃)₃ 364 2882,6-dichloro-4-pyridinyl 455 292 CH₂CH(CH₃)₂ * 293 CH₂CH₂CH₂CH₂CH₃ * 294CH₂CH₂CH₃ * 295 CH₂CH═CH₂ * 303 CH₂CH═CHC₆H₅ 424 309 1-naphthalenyl162-165 313 8-methyl-1-naphthalenyl 252-253 314 2-naphthalenyl 211-214331 5-bromo-3-pyridinyl * 341 CH═CHCH₂CH₃ 362 358 CH₂C≡CH * 3596-chloro-3-pyridinyl * 360 2-(2-chloro-4- 563(trifluoromethyl)phenyl)-4- pyridinyl 361 CH₂C≡CCH₃ * 371 H 308 3796-methyl-3-pyridinyl 399 383 cis-CH₂CH═CHCH₃ * 393 5-methyl-3-pyridinyl399 394 5-ethyl-3-pyridinyl 413 418 6-fluoro-3-pyridinyl 403 4192-chloro-3-pyridinyl 419 444 3-cyano-2-pyridinyl 410 4476-(4-(trifluoromethyl)phenyl)-3- 529 pyridinyl 454 2-thienyl 390 4553-thienyl 390 456 1-(2,6-dichloro-4- 586 (trifluoromethyl)phenyl-4-pyrazolyl) 461 2-(2-chloro-4- 563 (trifluoromethyl)phenyl)-3- pyridinyl465 4-bromo-2-thienyl 468 492 4-(2-chloro-4- 568(trifluoromethyl)phenyl)-2-thienyl * See Index Table F for ¹H NMR data.R^(B) is X-2; R^(3a), R^(3b) and R^(3c) are H; R^(3d) is CH₃

INDEX TABLE E m.p. AP+ Cmpd Structure (° C.) (M + 1) 91

337 92

321 93

331 94

365 95

402 96

* 97

432 98

* 99

420 100

452 171

438 172

487 333

387 334

565 340

455 356

224- 226 357

235- 236 391

510 * See Index Table F for ¹H NMR data.

INDEX TABLE F Cmpd No. ¹H NMR Data ^(a, b) 13 δ 9.47 (s, 1H), 8.39 (s,1H), 7.80-7.85 (m, 2H), 7.74 (s, 1H), 7.65 (s, 1H), 7.43 (t, 1H), 7.32(d, 1H), 7.14 (d, 1H), 5.75 (br s, 2H). 14 δ 9.43 (s, 1H), 8.39 (s, 1H),7.76-7.85 (m, 2H), 7.74 (s, 1H), 7.65 (s, 1H), 7.43 (t, 1H), 7.32 (d,1H), 7.14 (d, 1H), 5.75 (br s, 2H). 15 δ 9.47 (s, 1H), 8.39 (s, 1H),7.73-7.83 (m, 3H), 7.64 (dd, 1H), 7.30 (d, 1H), 7.11 (t, 2H), 5.75 (brs, 2H). 16 δ (CD₃OD) 9.85 (D, 1H), 7.56 (d, 2H), 7.49 (d, 1H), 7.32-7.38(m, 3H), 7.22 (t, 1H), 6.2 (br s, 2H). 42 δ (acetone-d₆) 9.46 (d, 1H),9.04 (s, 1H), 8.81 (s, 2H), 8.23 (d, 1H), 7.86 (d, 2H), 7.53 (t, 1H),7.26 (t, 2H), 7.11 (t, 1H), 5.65 (s, 2H), 2.68 (s, 3H). 43 δ(acetone-d₆) 9.47 (d, 1H), 9.05 (s, 1H), 8.83 (s, 2H), 8.27 (d, 1H),8.02-8.04 (m, 2H), 7.57 (t, 1H), 7.38 (t, 1H), 7.06 (d, 1H), 5.66 (s,2H), 2.69 (s, 3H). 44 δ (acetone-d₆) 9.41 (d, 1H), 9.04 (s, 1H), 8.79(s, 2H), 8.24 (d, 1H), 7.53 (m, 2H), 7.26 (m, 1H), 7.04-7.12 (m, 2H),5.65 (s, 2H), 2.68 (s, 3H). 45 δ (acetone-d₆) 9.46 (d, 1H), 9.05 (s,1H), 8.83 (s, 2H), 8.37 (s, 1H), 8.26 (d, 1H), 8.24 (d, 1H), 7.58 (t,1H), 7.43-7.51 (m, 2H), 5.67 (s, 2H), 2.69 (s, 3H). 46 δ (acetone-d₆)9.39 (d, 1H), 9.04 (s, 1H), 8.79 (s, 2H), 8.28 (d, 1H), 7.56 (t, 1H),7.34 (t, 1H), 6.96 (t, 2H), 5.67 (s, 2H), 2.72 (s, 3H). 96 δ 9.42 (d,1H), 8.3 (d, 1H), 7.73-7.9 (m, 4H), 7.68 (t, 1H), 7.39-7.48 (m, 3H),7.26 (m, 1H). 98 δ 9.31 (d, 1H), 8.43 (d, 1H), 8.22 (s, 1H), 7.97 (dd,2H), 7.80-7.85 (m, 2H), 7.72 (dd, 1H), 7.61 (2s, 2H), 7.38 (dd, 2H),7.07 (d, 1H), 5.72 (br s, 2H). 206 δ (DMSO-d₆) 9.27 (d, 1H), 8.29 (d,1H), 7.76 (s, 1H), 7.56 (t, 1H), 7.48 (dd, 1H), 7.41 (dd, 1H), 7.31-7.36(m, 2H), 5.46 (s, 2H) 2.73 (s, 3H). 218 δ 9.59 (d, 1H), 9.04 (d, 1H),7.84 (d,2H), 7.62 (s, 1H), 7.40 (dd, 1H), 7.30 (dd, 2H), 7.15 (dd, 1H),6.07 (s, 2H). 224 δ (acetone-d₆) 8.96 (d, 1H), 8.00 (s, 1H), 7.69-8.00(m, 4H), 7.26 (t, 1H), 6.91 (t, 1H), 5.61 (s, 2H), 2.55 (s, 3H). 225 δ(acetone-d₆) 9.41 (d, 1H), 8.39 (d, 1H), 8.28 (s, 1H), 8.12 (d, 1H),7.82 (d, 1H), 7.71 (s, 1H), 7.65 (t, 1H), 5.65 (s, 2H) 2.93 (s, 3H). 226δ 9.65 (d, 1H), 8.40 (d, 1H), 7.77 (d, 2H), 7.58 (s, 1H), 7.40 (dd, 3H),7.25 (dd, 1H), 5.62 (s, 2H), 5.39 (s, 2H), 2.24 (s, 3H). 237 δ(acetone-d₆) 9.44 (d, 1H), 8.34-8.37 (m, 2H), 8.14-8.21 (m, 3H), 7.74(s, 1H), 7.62 (t, 1H), 5.66 (s, 2H), 2.91 (s, 3H). 242 δ (acetone-d₆)9.31 (d, 1H), 8.40 (d, 1H), 7.67 (s, 1H), 7.61 t, 1H), 5.58 (s, 2H),2.81 (s, 3H). 260 δ (DMSO-d₆) 9.24 (d, 1H), 8.53 (d, 1H), 8.40 (t, 1H),8.16 (d, 1H), 7.99 (s, 1H), 7.57 (t, 2H), 7.46 (d, 2H), 7.37 (d, 2H),5.59 (s, 2H). 275 δ 9.48 (d, 1H), 7.94 (d, 1H), 7.42 (s, 1H), 7.33 (dd,1H), 5.60 (s, 2H), 2.80 (s, 3H), 2.14 (s, 3H). 280 δ 9.45 (d, 1H), 7.90(d, 1H), 7.41 (s, 1H), 7.30 (dd, 1H), 5.56 (s, 2H), 3.42 (m, 1H), 2.78(s, 3H), 1.34 (d, 6H). 281 δ 9.45 (d, 1H), 7.90 (d, 1H), 7.49 (d, 2H),7.39 (s, 1H), 7.24 (dd, 1 H), 7.22 (dd, 2H), 7.14 (dd, 1 H), 5.58 (s,2H), 3.96 (s, 2H), 2.76 (s, 3H). 282 δ 9.48 (d, 1H), 7.92 (d, 1H), 7.42(s, 1H), 7.29 (dd, 1H), 5.59 (s, 2H), 2.8 (s, 3H), 2.67 (q, 2H), 1.18(t, 3H). 292 δ 9.46 (d, 1H), 7.92 (d, 1H), 7.40 (s, 1H), 7.31 (dd, 1H),5.60 (s, 2H), 2.80 (s, 3H), 2.50 (d, 2H), 2.04 (m, 1H) 0.96 (d, 6H). 293δ 9.48 (d, 1H), 7.93 (d, 1H), 7.42 (s, 1H), 7.34 (dd, 1H), 5.58 (s, 2H),2.80 (s, 2H), 2.64 (d, 2H), 1.60 (m, 2H), 1.39 (m, 2H), 0.90 (t, 3H).294 δ 9.48 (d, 1H), 7.93 (d, 1H), 7.42 (s, 1H) 7.31 (dd, 1H), 5.58 (s,2H), 2.80 (s, 3H), 2.62 (m, 2H), 1.62 (m, 2H), 1.00 (t, 3H). 295 δ9.48(d, 1H), 7.94 (d, 1H), 7.41 (s, 1H), 7.32 (dd, 1H), 6.02 (m, 1H),5.60 (s, 2H), 5.21 (d 1H), 5.03 (d, 1H), 3.40 (d, 2H), 2.80 (s, 3H). 331δ (acetone-d₆) 9.47 (d, 1H), 9.21 (s, 1H), 8.60 (s, 1H), 8.42 (s, 1H),8.38 (d, 1H), 7.73 (s, 1H), 7.60 (t, 1H), 5.63 (s, 2H), 2.91 (s, 3H).335 δ (acetone-d₆) 9.46 (d, 1H), 7.99 (d, 1H), 7.82 (s, 1H), 7.37 (t,1H), 7.23 (s, 2H), 5.56 (s, 2H) 2.73 (s, 3H). 348 δ (DMSO-d₆) 9.33 (d,1H), 8.32 (d, 1H), 7.63 (d, 2H), 7.54 (s, 1H), 7.28 (t, 2H), 7.14 (t,1H), 7.00 (s, 1H), 6.70 (s, 1H), 6.24 (s, 2H), 2.61 (s, 3H), 2.26 (s,3H). 349 δ (DMSO-d₆) 9.32 (d, 1H), 8.30 (d, 1H), 7.71-7.65 (m, 2H), 7.60(t, 2H), 7.30 (t, 2H), 7.16 (t, 1H), 6.86 (s, 1H), 6.28 (s, 2H), 2.61(s, 3H), 2.02 (s, 3H). 358 δ 9.48 (d, 1H), 7.97 (d, 1H), 7.42 (s, 1H),7.36 (dd, 1H), 5.60 (s, 2H), 3.57 (s, 2H), 2.80 (s, 3H), 1.97 (s, 1H).359 δ (DMSO-d₆) 9.37 (d, 1H), 8.84 (s, 1H), 8.32-8.27 (m, 2H), 7.78 (s,1H), 7.59 (t, 1H), 7.49 (d, 1H), 5.44 (s, 2H), 2.70 (s, 3H). 361 δ 9.47(d, 1H), 7.96 (d, 1H), 7.42 (s, 1H), 7.35 (dd, 1H), 5.59 (s, 2H), 3.50(q, 2H), 2.80 (s, 3H), 1.77 (t, 3H). 383 δ 9.46 (d, 1H), 7.92 (d, 1H),7.40 (s, 1H), 7.31 (dd, 1H), 5.60 (m, 4H), 3.40 (d, 2H), 2.80 (s, 3H),1.83 (d, 3H). 488 δ (methanol-d₄) 9.37 (d, 1H), 8.29 (d, 1H), 7.63 (s,1H), 7.57-7.56 (m, 2H), 7.54- 7.50 (m, 1H), 5.60 (s, 2H), 2.81 (s, 3H).^(a) ¹H NMR data are in ppm downfield from tetramethylsilane. CDCl₃solution unless indicated otherwise; “acetone-d₆” is CD₃C(═O)CD₃.Couplings are designated by (s)—singlet, (d)—doublet, (t)—triplet,(m)—multiplet, (dd)—doublet of doublets, (br s)—broad singlet, ^(b) ¹HNMR spectra of compounds wherein R² is CH₂CF₃ often do not show peakscorresponding to the CH ₂CF₃ protons.

The following Tests demonstrate the control efficacy of compounds ofthis invention on specific pests. “Control efficacy” representsinhibition of invertebrate pest development (including mortality) thatcauses significantly reduced feeding. The pest control protectionafforded by the compounds is not limited, however, to these species.Compound numbers refer to compounds in Index Tables A-E.

Biological Examples of the Invention Test A

For evaluating control of diamondback moth (Plutella xylostella) thetest unit consisted of a small open container with a 12-14-day-oldradish plant inside. This was pre-infested with ˜50 neonate larvae thatwere dispensed into the test unit via corn cob grits using a bazookainoculator. The larvae moved onto the test plant after being dispensedinto the test unit.

Test compounds were formulated using a solution containing 10% acetone,90% water and 300 ppm X-77® Spreader Lo-Foam Formula non-ionicsurfactant containing alkylarylpolyoxyethylene, free fatty acids,glycols and isopropanol (Loveland Industries, Inc. Greeley, Colo., USA).The formulated compounds were applied in 1 mL of liquid through a SUJ2atomizer nozzle with ⅛ JJ custom body (Spraying Systems Co., Wheaton,Ill., USA) positioned 1.27 cm (0.5 inches) above the top of each testunit. Test compounds were sprayed at 50 ppm and/or 10 ppm, andreplicated three times. After spraying of the formulated test compound,each test unit was allowed to dry for 1 h and then a black, screened capwas placed on top. The test units were held for 6 days in a growthchamber at 25° C. and 70% relative humidity. Plant feeding damage wasthen visually assessed based on foliage consumed.

Of the compounds of Formula 1 tested at 50 ppm, the following providedvery good to excellent levels of control efficacy (40% or less feedingdamage and/or 100% mortality): 1, 18, 19, 20, 21, 23, 26, 28, 29, 30,33, 36, 37, 39, 40, 41, 43, 47, 48, 49, 50, 51, 52, 53, 54, 56, 57, 58,59, 60, 62, 63, 65, 66, 67, 70, 71, 72, 73, 74, 75, 77, 79, 80, 81, 82,83, 84, 85, 86, 87, 88, 89, 90, 99, 101, 102, 103, 104, 105, 106, 107,108, 110, 111, 112, 113, 114, 115, 116, 117, 118, 119, 120, 121, 122,123, 124, 125, 126, 127, 128, 129, 130, 131, 132, 133, 134, 135, 136,137, 138, 139, 140, 150, 151, 152, 153, 154, 155, 156, 157, 158, 159,160, 161, 162, 163, 164, 165, 166, 167, 168, 169, 170, 172, 173, 174,175, 176, 177, 178, 179, 180, 181, 182, 183, 184, 186, 187, 188, 189,190, 191, 192, 193, 194, 195, 196, 198, 199, 200, 201, 202, 203, 204,205, 206, 207, 208, 209, 210, 211, 212, 214, 215, 217, 218, 219, 220,221, 222, 223, 225, 227, 228, 229, 230, 231, 232, 235, 236, 237, 238,239, 240, 241, 242, 244, 245, 246, 248, 250, 251, 252, 253, 254, 255,256, 257, 258, 259, 261, 262, 263, 264, 265, 266, 267, 268, 269, 270,271, 272, 273, 274, 275, 276, 277, 278, 279, 280, 281, 282, 283, 285,286, 287, 288, 289, 290, 291, 292, 293, 294, 295, 296, 297, 298, 299,300, 301, 302, 304, 305, 306, 307, 308, 309, 310, 311, 312, 314, 315,316, 317, 318, 319 and 334.

Of the compounds of Formula 1 tested at 10 ppm, the following providedvery good to excellent levels of control efficacy (40% or less feedingdamage and/or 100% mortality): 1, 18, 20, 21, 23, 26, 29, 30, 33, 36,37, 39, 40, 41, 47, 48, 49, 50, 51, 52, 53, 54, 56, 57, 58, 59, 60, 62,63, 65, 66, 70, 71, 72, 73, 74, 79, 80, 81, 82, 83, 84, 85, 86, 89, 90,99, 101, 102, 103, 104, 105, 106, 110, 111, 112, 113, 114, 115, 117,118, 119, 120, 121, 122, 123, 124, 125, 126, 127, 128, 129, 130, 131,132, 133, 134, 135, 136, 137, 138, 139, 140, 150, 151, 152, 154, 156,157, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 169, 170,171, 173, 175, 176, 177, 178, 179, 180, 181, 182, 183, 184, 185, 186,187, 188, 189, 190, 191, 193, 194, 195, 196, 198, 199, 200, 201, 203,205, 206, 207, 208, 209, 210, 211, 212, 214, 215, 216, 217, 218, 219,220, 221, 223, 225, 227, 228, 229, 230, 231, 235, 236, 237, 238, 239,240, 241, 242, 244, 245, 246, 248, 250, 251, 252, 253, 254, 255, 256,257, 259, 261, 262, 263, 265, 266, 267, 269, 270, 271, 272, 273, 274,276, 277, 278, 280, 281, 285, 286, 287, 288, 289, 290, 291, 292, 294,295, 296, 297, 298, 299, 300, 301, 302, 304, 305, 306, 307, 308, 309,310, 311, 312, 314, 315, 316, 317, 318, 319, 321, 322, 323, 324, 325,326, 327, 328, 329, 330, 331, 332, 334, 335, 336, 337, 338, 339, 340,341, 342, 343, 344, 345, 346, 347, 351, 352, 353, 354, 355, 356, 357,359, 360, 363, 364, 365, 366, 367, 368, 369, 373, 374, 375, 376, 377,378, 379, 380, 381, 382, 383, 384, 385, 386, 387, 388, 395, 397, 398,399, 400, 401, 402, 403, 404, 405, 407, 408, 409, 411, 412, 414, 415,416, 419, 421, 422, 423, 424, 425, 426, 427, 429, 431, 432, 433, 434,435, 437, 438, 439, 440, 441, 442, 443, 445, 448, 449, 450, 451, 452,453, 454, 455, 457, 459, 462, 464, 465, 466, 467, 468, 469, 470, 474,475, 476, 477, 478, 479, 481, 482, 483, 484, 485, 486, 487, 488, 489,490, 491, 492, 493, 495, 496, 497, 498, 499, 500 and 501.

Test B

For evaluating control of fall armyworm (Spodoptera frugiperda) the testunit consisted of a small open container with a 4-5-day-old maize (corn)plant inside. This was pre-infested (using a core sampler) with 10-151-day-old larvae on a piece of insect diet.

Test compounds were formulated and sprayed at 50 ppm and/or 10 ppm asdescribed for Test A. The applications were replicated three times.After spraying, the test units were maintained in a growth chamber at25° C. and 70% relative humidity and then visually rated as describedfor Test A.

Of the compounds of Formula 1 tested at 50 ppm, the following providedvery good to excellent levels of control efficacy (40% or less feedingdamage and/or 100% mortality): 1, 18, 19, 20, 21, 23, 26, 29, 30, 33,36, 37, 40, 47, 49, 50, 51, 52, 53, 54, 56, 57, 58, 59, 60, 62, 63, 65,66, 71, 74, 79, 80, 81, 82, 83, 84, 85, 86, 87, 89, 90, 101, 102, 103,104, 105, 106, 110, 111, 112, 113, 115, 117, 118, 119, 120, 121, 122,123, 124, 125, 126, 127, 128, 129, 130, 131, 132, 133, 134, 135, 136,137, 138, 139, 140, 150, 151, 152, 154, 157, 158, 159, 160, 161, 162,163, 164, 165, 166, 167, 168, 170, 171, 172, 173, 174, 175, 176, 177,178, 179, 180, 181, 182, 183, 184, 187, 188, 189, 190, 191, 192, 193,194, 195, 196, 198, 199, 200, 201, 202, 203, 205, 207, 208, 209, 210,211, 214, 215, 219, 220, 221, 223, 227, 228, 229, 230, 231, 232, 235,236, 238, 239, 240, 241, 244, 245, 246, 248, 250, 251, 252, 253, 254,255, 256, 257, 259, 261, 262, 263, 264, 265, 266, 267, 269, 270, 271,272, 273, 274, 276, 277, 278, 279, 281, 285, 286, 288, 289, 290, 291,292, 294, 296, 297, 299, 300, 301, 304, 305, 306, 307, 308, 309, 310,311, 313, 314, 315, 316, 317, 318, 319 and 334.

Of the compounds of Formula 1 tested at 10 ppm, the following providedvery good to excellent levels of control efficacy (40% or less feedingdamage and/or 100% mortality): 1, 18, 20, 23, 26, 29, 30, 33, 36, 40,47, 49, 50, 51, 52, 53, 57, 58, 59, 60, 62, 63, 65, 66, 71, 79, 80, 81,82, 83, 84, 85, 86, 89, 90, 101, 102, 103, 105, 113, 115, 118, 120, 121,122, 123, 125, 126, 127, 128, 131, 132, 133, 134, 135, 136, 137, 138,139, 140, 150, 151, 152, 154, 157, 158, 159, 160, 161, 162, 163, 165,167, 168, 170, 173, 174, 175, 176, 177, 178, 180, 183, 184, 187, 189,190, 191, 193, 194, 195, 196, 198, 199, 200, 202, 203, 207, 208, 209,210, 211, 214, 215, 219, 220, 227, 228, 229, 230, 231, 232, 235, 238,239, 240, 241, 244, 245, 246, 248, 250, 251, 252, 253, 254, 255, 256,257, 261, 262, 263, 264, 265, 266, 269, 270, 271, 272, 276, 277, 278,285, 286, 288, 289, 290, 291, 296, 297, 299, 300, 301, 305, 307, 308,309, 313, 314, 315, 316, 317, 321, 322, 323, 325, 326, 327, 329, 330,332, 334, 335, 336, 337, 338, 341, 343, 344, 345, 346, 347, 351, 352,353, 354, 355, 359, 363, 364, 365, 366, 367, 368, 369, 374, 375, 376,377, 378, 380, 381, 382, 384, 385, 386, 387, 388, 391, 395, 398, 399,401, 402, 403, 404, 405, 407, 408, 409, 410, 411, 412, 413, 414, 415,421, 422, 424, 425, 426, 427, 429, 431, 432, 433, 434, 435, 437, 438,439, 440, 441, 442, 443, 448, 449, 450, 451, 453, 454, 455, 457, 458,462, 464, 465, 466, 467, 468, 479, 480, 481, 482, 483, 484, 485, 486,487, 489, 490, 491, 492, 493, 495, 496, 497, 498, 499, 500 and 501.

Test C

For evaluating control of green peach aphid (Myzus persicae) throughcontact and/or systemic means, the test unit consisted of a small opencontainer with a 12-15-day-old radish plant inside. This waspre-infested by placing on a leaf of the test plant 30-40 aphids on apiece of leaf excised from a culture plant (cut-leaf method). The aphidsmoved onto the test plant as the leaf piece desiccated. Afterpre-infestation, the soil of the test unit was covered with a layer ofsand.

Test compounds were formulated and sprayed at 50 ppm and/or 10 ppm asdescribed for Test A. The applications were replicated three times.After spraying of the formulated test compound, each test unit wasallowed to dry for 1 h and then a black, screened cap was placed on top.The test units were held for 6 days in a growth chamber at 19-21° C. and50-70% relative humidity. Each test unit was then visually assessed forinsect mortality.

Of the compounds of Formula 1 tested at 50 ppm, the following resultedin at least 80% mortality: 29, 30, 32, 36, 40, 45, 47, 48, 50, 53, 56,59, 60, 62, 71, 73, 74, 79, 80, 81, 82, 83, 85, 89, 102, 103, 104, 105,111, 112, 113, 114, 115, 117, 118, 119, 120, 121, 122, 123, 125, 131,132, 133, 135, 156, 159, 160, 167, 168, 173, 180, 182, 183, 191, 196,199, 203, 205, 209, 211, 227, 228, 238, 239, 240, 241, 245, 257, 261,265, 266, 270, 272, 275, 278, 280, 282, 285, 288, 289, 291, 294, 295,296, 299, 304, 308, 311, 312, 324, 330, 331, 333, 337, 340, 343, 357,358, 359, 360, 361, 364, 367, 368, 369, 372, 373, 374, 376, 378, 382,383, 393, 395, 399, 403, 404, 405, 409, 411, 412, 414, 419, 421, 424,425, 432, 435, 438, 439, 441, 443, 453, 457, 478, 495, 498 and 499.

Of the compounds of Formula 1 tested at 10 ppm, the following resultedin at least 80% mortality: 29, 30, 36, 47, 50, 53, 59, 62, 74, 79, 80,81, 83, 113, 115, 118, 120, 121, 122, 123, 125, 132, 133, 135, 159, 160,168, 180, 182, 183, 227, 240, 241, 257, 266, 285, 288, 289, 294, 295,296, 299, 304, 311, 331, 333, 359, 374, 382, 395, 405, 424, 438, 439,453, 495 and 498.

Test D

For evaluating control of cotton melon aphid (Aphis gossypii) throughcontact and/or systemic means, the test unit consisted of a small opencontainer with a 6-7-day-old cotton plant inside. This was pre-infestedwith 30-40 insects on a piece of leaf according to the cut-leaf methoddescribed for Test C, and the soil of the test unit was covered with alayer of sand.

Test compounds were formulated and sprayed at 50 ppm and/or 10 ppm asdescribed for Test C. The applications were replicated three times.After spraying, the test units were maintained in a growth chamber andthen visually rated as described for Test C.

Of the compounds of Formula 1 tested at 50 ppm, the following resultedin at least 80% mortality: 30, 36, 40, 48, 50, 53, 60, 62, 73, 74, 79,80, 81, 82, 83, 102, 111, 115, 118, 121, 122, 123, 124, 125, 126, 129,131, 133, 135, 159, 168, 180, 182, 183, 196, 199, 227, 235, 240, 257,266, 275, 296, 304, 331, 333, 339, 340, 351, 373, 395, 405, 424, 425,439, 441, 478, 495 and 498.

Of the compounds of Formula 1 tested at 10 ppm, the following resultedin at least 80% mortality: 53, 60, 62, 79, 83, 121, 122, 123, 168, 180,182, 227, 240, 266, 296, 340, 373, 424, 495 and 498.

Test E

For evaluating control of corn planthopper (Peregrinus maidis) throughcontact and/or systemic means, the test unit consisted of a small opencontainer with a 3-4-day-old maize plant (spike) inside. White sand wasadded to the top of the soil prior to application. Test compounds wereformulated and sprayed at 50 ppm and/or 10 ppm, and replicated threetimes as described for Test A. After spraying, the test units wereallowed to dry for 1 h before they were post-infested with ˜15-20 nymphs(18 to 21 day old) by sprinkling them onto the sand with a salt shaker.A black, screened cap was placed on the top of each test unit, and thetest units were held for 6 days in a growth chamber at 22-24° C. and50-70% relative humidity. Each test unit was then visually assessed forinsect mortality.

Of the compounds of Formula 1 tested at 50 ppm the following providedvery good to excellent levels of control efficacy (80% or moremortality): 1, 21, 26, 29, 30, 36, 40, 44, 47, 48, 49, 50, 51, 52, 53,56, 57, 59, 60, 62, 63, 65, 70, 71, 73, 74, 77, 79, 80, 81, 82, 83, 84,85, 101, 102, 103, 105, 111, 112, 113, 114, 115, 116, 117, 118, 119,120, 121, 122, 123, 124, 125, 126, 127, 128, 129, 130, 131, 132, 133,134, 135, 152, 157, 158, 159, 160, 165, 167, 168, 170, 173, 180, 181,182, 183, 189, 191, 196, 199, 203, 205, 206, 209, 212, 227, 228, 231,235, 240, 242, 246, 254, 257, 261, 262, 272, 275, 277, 282, 288, 289,291, 294, 295, 296, 297, 298, 299, 300, 304, 309, 311, 312, 322, 324,330, 331, 333, 337, 339, 340, 342, 343, 344, 347, 349, 352, 355, 358,359, 360, 361, 363, 364, 365, 368, 369, 372, 373, 374, 377, 378, 379,382, 384, 387, 393, 394, 395, 397, 399, 404, 405, 409, 414, 419, 421,422, 424, 425, 432, 435, 439, 443, 450, 452, 453, 454, 455, 462, 464,467, 475, 478, 482, 495, 496, 497, 498, 499 and 501.

Of the compounds of Formula 1 tested at 10 ppm the following providedvery good to excellent levels of control efficacy (80% or moremortality): 26, 29, 30, 36, 37, 47, 48, 49, 50, 53, 56, 57, 59, 60, 62,63, 74, 79, 80, 81, 82, 84, 102, 103, 105, 112, 113, 114, 115, 118, 119,120, 121, 122, 123, 124, 125, 126, 127, 128, 129, 130, 132, 133, 135,152, 157, 158, 159, 160, 165, 167, 168, 170, 173, 180, 182, 183, 189,196, 227, 235, 240, 246, 257, 275, 282, 288, 289, 295, 296, 299, 300,304, 309, 311, 324, 331, 333, 339, 340, 342, 358, 359, 364, 373, 374,382, 393, 395, 397, 405, 419, 424, 452, 453, 455, 467, 478, 495, 496,498 and 499.

Test F

For evaluating control of potato leafhopper (Empoasca fabae) throughcontact and/or systemic means, the test unit consisted of a small opencontainer with a 5-6-day-old Soleil bean plant (primary leaves emerged)inside. White sand was added to the top of the soil and one of theprimary leaves was excised prior to application.

Test compounds were formulated and sprayed at 50 ppm and/or 10 ppm, andthe tests were replicated three times as described for Test A. Afterspraying, the test units were allowed to dry for 1 h before they werepost-infested with 5 potato leafhoppers (18-21-day-old adults). A black,screened cap was placed on the top of each test unit, and the test unitswere held for 6 days in a growth chamber at 24° C. and 70% relativehumidity. Each test unit was then visually assessed for insectmortality.

Of the compounds of Formula 1 tested at 50 ppm the following providedvery good to excellent levels of control efficacy (80% or moremortality): 1, 20, 21, 23, 26, 29, 30, 36, 37, 40, 41, 42, 43, 44, 45,47, 48, 49, 50, 51, 52, 53, 56, 57, 58, 59, 60, 62, 63, 65, 66, 71, 74,75, 77, 79, 80, 81, 82, 83, 84, 85, 89, 104, 105, 106, 107, 110, 111,112, 113, 114, 115, 116, 117, 118, 119, 120, 121, 122, 123, 124, 125,126, 127, 128, 129, 130, 131, 132, 134, 135, 136, 139, 140, 150, 152,153, 155, 156, 157, 158, 159, 160, 161, 164, 165, 166, 167, 168, 169,170, 173, 179, 180, 181, 182, 183, 186, 188, 189, 191, 193, 196, 199,204, 205, 206, 207, 209, 210, 211, 212, 214, 215, 218, 225, 226, 227,228, 230, 231, 235, 236, 238, 239, 240, 242, 245, 246, 250, 251, 256,257, 261, 262, 272, 275, 276, 277, 278, 280, 282, 285, 286, 288, 289,291, 292, 294, 295, 296, 299, 300, 301, 302, 304, 305, 306, 308, 309,310, 311, 312, 318, 321, 322, 323, 324, 325, 327, 328, 330, 333, 336,337, 338, 340, 342, 343, 344, 352, 354, 355, 356, 357, 358, 359, 360,361, 363, 364, 367, 368, 369, 372, 373, 374, 375, 376, 377, 378, 382,384, 385, 387, 388, 403, 404, 405, 407, 412, 414, 419, 421, 424, 425,427, 432, 435, 438, 439, 440, 441, 443, 450, 457, 464, 467, 478, 482,495, 498 and 499.

Of the compounds of Formula 1 tested at 10 ppm the following providedvery good to excellent levels of control efficacy (80% or moremortality): 26, 29, 30, 36, 37, 40, 47, 48, 49, 50, 51, 52, 53, 56, 57,59, 60, 62, 63, 65, 66, 71, 75, 79, 80, 81, 82, 83, 84, 88, 89, 102,104, 105, 106, 111, 113, 114, 115, 116, 118, 119, 120, 121, 122, 123,124, 125, 126, 127, 129, 130, 131, 132, 135, 152, 157, 158, 159, 160,161, 164, 165, 166, 168, 169, 170, 173, 180, 182, 183, 189, 191, 196,205, 206, 210, 211, 212, 214, 218, 227, 228, 231, 236, 239, 240, 245,246, 256, 257, 262, 272, 277, 282, 285, 286, 289, 291, 295, 299, 300,302, 309, 310, 312, 322, 323, 324, 330, 333, 342, 343, 344, 352, 354,357, 359, 360, 364, 367, 368, 374, 375, 382, 405, 424, 434, 438, 440,443, 478, 498 and 499.

Test G

For evaluating control of Western Flower Thrips (Frankliniellaoccidentalis) through contact and/or systemic means, the test unitconsisted of a small open container with a 5-7-day-old Soleil bean plantinside.

Test compounds were formulated and sprayed at 250, 50 and/or 10 ppm, andthe tests were replicated three times as described for Test A. Afterspraying, the test units were allowed to dry for 1 hour, and then 22-27adult thrips were added to the unit. A black, screened cap was placed onthe top of each test unit, and the test units were held for 7 days at25° C. and 45-55% relative humidity.

Of the compounds of Formula 1 tested at 250 ppm, the following providedvery good to excellent levels of control efficacy (30% or less plantdamage and/or 100% mortality): 50, 56, 89, 121, 139, 343, 344 and 346.

Of the compounds of Formula 1 tested at 50 ppm, the following providedvery good to excellent levels of control efficacy (30% or less plantdamage and/or 100% mortality): 191, 199, 230, 272, 285, 289, 300, 321,322, 343, 344, 346, 352, 360, 364, 365, 368, 369, 377, 378, 407, 409,411, 421, 432, 435, 438, 440 and 443.

Of the compounds of Formula 1 tested at 10 ppm, the following providedvery good to excellent levels of control efficacy (30% or less plantdamage and/or 100% mortality): 272, 289, 343, 344, 346, 364 and 369.

What is claimed is:
 1. A composition comprising a compound of Formula 1or salt thereof,

wherein X is O or S; Y is O or S; A is C(R^(3c))═C(R^(3d)), providedthat the C(R^(3c))═C(R^(3d)) moiety is oriented so the carbon atombonded to R^(3d) is connected directly to the pyrimidinium ring ofFormula 1; Z is a direct bond, O, S(O)_(n), NR⁶, C(R⁷)₂O, OC(R⁷)₂,C(═X¹), C(═X¹)E, EC(═X¹), C(═NOR⁸) or C(═NN(R⁶)₂); X¹ is O, S or NR⁹; Eis O, S or NR^(9a); R¹ is a 3- to 10-membered ring or a 7- to11-membered ring system, each ring or ring system containing ringmembers selected from carbon atoms and up to 4 heteroatoms independentlyselected from up to 2 O, up to 2 S, and up to 4 N, wherein up to 3carbon atom ring members are independently selected from C(═O) and C(═S)and the sulfur atom ring members are independently selected fromS(═O)_(u)(═NR²⁴)_(z), each ring or ring system optionally substitutedwith up to 5 substituents independently selected from R¹⁴; R² is H,halogen, cyano, hydroxy, amino, nitro, OCN, SCN, CHO, C(═O)OH, C(═O)NH₂,C(═S)NH₂, SO₂NH₂, C(═O)R¹⁸, C(═O)OR¹⁸, NHR¹⁸, NR¹⁸R¹⁹, C(═O)NR²¹R¹⁹,C(═S)NR²¹R¹⁹, SO₂NR²¹R¹⁹, OC(═O)R²¹, OC(═O)OR¹⁸, OC(═O)NR²¹R¹⁹,N(R²¹)C(═O)R²¹, N(R²¹)C(═O)OR¹⁹, N(R²¹)C(═O)NR²¹R²², OSO₂R¹⁸,OSO₂NR²¹R²², NR²¹SO₂R¹⁸, NR²¹SO₂NR²¹R²² or Si(R¹⁸R¹⁹R²⁰); or C₁-C₈alkyl, C₂-C₈ alkenyl, C₂-C₈ alkynyl, C₃-C₁₀ cycloalkyl, C₄-C₁₀alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₆-C₁₄ cycloalkylcycloalkyl,C₅-C₁₀ alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl, C₁-C₈ alkoxy, C₃-C₈cycloalkoxy, C₄-C₁₀ cycloalkylalkoxy, C₂-C₈ alkenyloxy, C₂-C₈alkynyloxy, C₁-C₈ alkylthio, C₁-C₈ alkylsulfinyl, C₁-C₈ alkylsulfonyl,C₃-C₈ cycloalkylthio, C₃-C₈ cycloalkylsulfinyl, C₃-C₈cycloalkylsulfonyl, C₄-C₁₀ cycloalkylalkylthio, C₄-C₁₀cycloalkylalkylsulfinyl, C₄-C₁₀ cycloalkylalkylsulfonyl, C₂-C₈alkenylthio, C₂-C₈ alkenylsulfinyl, C₂-C₈ alkenylsulfonyl, C₂-C₈alkynylthio, C₂-C₈ alkynylsulfinyl or C₂-C₈ alkynylsulfonyl, eachunsubstituted or substituted with at least one substituent independentlyselected from the group consisting of halogen, cyano, nitro, CHO,C(═O)OH, C(═O)NH₂, C(═O)R¹⁰, C(═O)OR¹¹, C(═O)NR¹²R¹³, OR¹¹, S(O)_(n)R¹⁰SO₂NR¹²R¹³ and Si(R¹⁰)₃; or a 3- to 10-membered ring or a 7- to11-membered ring system, each ring or ring system containing ringmembers selected from carbon atoms and up to 4 heteroatoms independentlyselected from up to 2 O, up to 2 S, and up to 4 N, wherein up to 3carbon atom ring members are independently selected from C(═O) and C(═S)and the sulfur atom ring members are independently selected fromS(═O)_(u)(═NR²⁴)_(z), each ring or ring system optionally substitutedwith up to 5 substituents independently selected from R¹⁵; R^(3a),R^(3b), R^(3c) and R^(3d) are independently H, halogen, cyano, hydroxy,amino, nitro, SF₅, OCN, SCN, CHO, C(═O)OH, C(═O)NH₂, C(═S)NH₂, SO₂NH₂,C(═O)R¹⁸, C(═O)OR¹⁸, NHR¹⁸, NR¹⁸R¹⁹, C(═O)NR²¹R¹⁹, C(═S)NR²¹R¹⁹,SO₂NR²¹R¹⁹ OC(═O)R²¹, OC(═O)OR¹⁸, OC(═O)NR²¹R¹⁹, N(R²¹)C(═O)R²¹,N(R²¹)C(═O)OR¹⁹, N(R²¹)C(═O)NR²¹R²², OSO₂R¹⁸, OSO₂NR²¹R²², NR²¹SO₂R¹⁸,NR²¹SO₂NR²¹R²², Si(R¹⁸R¹⁹R²⁰) or Z¹Q^(t); or C₁-C₈ alkyl, C₂-C₈ alkenyl,C₂-C₈ alkynyl, C₃-C₁₀ cycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀cycloalkylalkyl, C₆-C₁₄ cycloalkylcycloalkyl, C₅-C₁₀alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl, C₁-C₈ alkoxy, C₃-C₈cycloalkoxy, C₄-C₁₀ cycloalkylalkoxy, C₂-C₈ alkenyloxy, C₂-C₈alkynyloxy, C₁-C₈ alkylthio, C₁-C₈ alkylsulfinyl, C₁-C₈ alkylsulfonyl,C₃-C₈ cycloalkylthio, C₃-C₈ cycloalkylsulfinyl, C₃-C₈cycloalkylsulfonyl, C₄-C₁₀ cycloalkylalkylthio, C₄-C₁₀cycloalkylalkylsulfinyl, C₄-C₁₀ cycloalkylalkylsulfonyl, C₂-C₈alkenylthio, C₂-C₈ alkenylsulfinyl, C₂-C₈ alkenylsulfonyl, C₂-C₈alkynylthio, C₂-C₈ alkynylsulfinyl or C₂-C₈ alkynylsulfonyl, eachunsubstituted or substituted with at least one substituent independentlyselected from R¹⁷; or R^(3a) and R^(3b), or R^(3b) and R^(3c), or R^(3c)and R^(3d) are taken together with the adjacent carbon atoms to whichthey are attached to form a 5- to 7-membered carbocyclic or heterocyclicring, each ring containing ring members selected from carbon atoms andup to 3 heteroatoms independently selected from up to 2 O, up to 2 S,and up to 3 N, wherein up to 2 carbon atom ring members areindependently selected from C(═O) and C(═S) and the sulfur atom ringmembers are independently selected from S(═O)_(n), each ring optionallysubstituted with up to 3 substituents independently selected from thegroup consisting of halogen, cyano, hydroxy, amino, nitro, C(═O)OH,C(═O)NH₂, SO₂NH₂, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄haloalkenyl, C₂-C₄ alkynyl, C₂-C₄ haloalkynyl, C₃-C₇ cycloalkyl, C₃-C₇halocycloalkyl, C₄-C₈ alkylcycloalkyl, C₄-C₈ haloalkylcycloalkyl, C₄-C₈cycloalkylalkyl, C₄-C₈ halocycloalkylalkyl, C₁-C₆ alkoxy, C₁-C₆haloalkoxy, C₂-C₆ alkoxycarbonyl, C₂-C₆ haloalkoxycarbonyl, C₂-C₆alkylcarbonyl and C₂-C₆ haloalkylcarbonyl; each R⁴ and R⁵ isindependently H, halogen, cyano, hydroxy, amino, nitro, OCN, SCN, CHO,C(═O)OH, C(═O)NH₂, C(═S)NH₂ or SO₂NH₂; or C₁-C₆ alkyl, C₂-C₆ alkenyl,C₂-C₆ alkynyl, C₃-C₈ cycloalkyl, C₄-C₈ alkylcycloalkyl, C₄-C₈cycloalkylalkyl, C₆-C₁₂ cycloalkylcycloalkyl, C₅-C₈alkylcycloalkylalkyl, C₃-C₆ cycloalkenyl, C₁-C₆ alkoxy, C₃-C₆cycloalkoxy, C₄-C₈ cycloalkylalkoxy, C₂-C₆ alkenyloxy or C₂-C₆alkynyloxy, each unsubstituted or substituted with at least onesubstituent independently selected from the group consisting of halogen,cyano, nitro, CHO, C(═O)OH, C(═O)NH₂, C(═O)R¹⁰, C(═O)OR¹¹, C(═O)NR¹²R¹³,OR¹¹, S(O)_(n)R¹⁰, SO₂NR¹²R¹³ and Si(R¹⁰)₃; or R⁴ and R⁵ are takentogether with the carbon atom to which they are attached to form a 3- to7-membered ring containing ring members selected from carbon atoms andup to 2 heteroatoms independently selected from one O, one S, and up to2 N, wherein up to 2 carbon atom ring members are independently selectedfrom C(═O) and C(═S) and the sulfur atom ring member is selected from S,S(O) or S(O)₂, said ring optionally substituted with up to 4substituents independently selected from the group consisting ofhalogen, cyano and C₁-C₄ alkyl; each R⁶ is independently H; or C₁-C₆alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₈ cycloalkyl, C₄-C₈alkylcycloalkyl, C₄-C₈ cycloalkylalkyl, C₆-C₁₀ cycloalkylcycloalkyl,C₅-C₁₀ alkylcycloalkylalkyl, C₃-C₆ cycloalkenyl, C₂-C₆ alkylcarbonyl orC₂-C₆ alkoxycarbonyl, each unsubstituted or substituted with at leastone substituent independently selected from the group consisting ofhalogen, cyano, nitro, CHO, C(═O)OH, C(═O)NH₂, C(═O)R¹⁰, C(═O)OR¹¹,C(═O)NR¹²R¹³, OR¹¹, S(O)_(n)R¹⁰, SO₂NR¹²R¹³ and Si(R¹⁰)₃; or two R⁶substituents are taken together with the nitrogen atom to which they areattached to form a 3- to 7-membered ring containing ring membersselected from carbon atoms and up to 2 heteroatoms independentlyselected from one O, one S, and up to 2 N, wherein up to 2 carbon atomring members are independently selected from C(═O) and C(═S) and thesulfur atom ring member is selected from S, S(O) or S(O)₂, said ringoptionally substituted with up to 4 substituents independently selectedfrom the group consisting of halogen, cyano and C₁-C₄ alkyl; each R⁷ andR⁸ is independently H; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl,C₃-C₈ cycloalkyl, C₄-C₈ alkylcycloalkyl, C₄-C₈ cycloalkylalkyl, C₆-C₁₀cycloalkylcycloalkyl, C₅-C₁₀ alkylcycloalkylalkyl, C₃-C₆ cycloalkenyl,C₂-C₆ alkylcarbonyl or C₂-C₆ alkoxycarbonyl, each unsubstituted orsubstituted with at least one substituent independently selected fromthe group consisting of halogen, cyano, nitro, CHO, C(═O)OH, C(═O)NH₂,C(═O)R¹⁰, C(═O)OR¹¹, C(═O)NR¹²R¹³, OR¹¹, S(O)_(n)R¹⁰, SO₂NR¹²R¹³ andSi(R¹⁰)₃; each R⁹ is independently C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆alkynyl, C₃-C₈ cycloalkyl, C₄-C₈ alkylcycloalkyl, C₄-C₈ cycloalkylalkyl,C₆-C₁₀ cycloalkylcycloalkyl, C₅-C₁₀ alkylcycloalkylalkyl, C₃-C₆cycloalkenyl, C₂-C₆ alkylcarbonyl or C₂-C₆ alkoxycarbonyl, eachunsubstituted or substituted with at least one substituent independentlyselected from the group consisting of halogen, cyano, nitro, CHO,C(═O)OH, C(═O)NH₂, C(═O)R¹⁰, C(═O)OR¹¹, C(═O)NR¹²R¹³, OR¹¹, S(O)_(n)R¹⁰,SO₂NR¹²R¹³ and Si(R¹⁰)₃; each R^(9a) is independently H; or C₁-C₆ alkyl,C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₈ cycloalkyl, C₄-C₈ alkylcycloalkyl,C₄-C₈ cycloalkylalkyl, C₆-C₁₀ cycloalkylcycloalkyl, C₅-C₁₀alkylcycloalkylalkyl, C₃-C₆ cycloalkenyl, C₂-C₆ alkylcarbonyl or C₂-C₆alkoxycarbonyl, each unsubstituted or substituted with at least onesubstituent independently selected from the group consisting of halogen,cyano, nitro, CHO, C(═O)OH, C(═O)NH₂, C(═O)R¹⁰, C(═O)OR¹¹, C(═O)NR¹²R¹³,OR¹¹, S(O)_(n)R¹⁰, SO₂NR¹²R¹³ and Si(R¹⁰)₃; each R¹⁰ and R¹¹ isindependently C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₈cycloalkyl, C₄-C₈ alkylcycloalkyl, C₄-C₈ cycloalkylalkyl, C₆-C₁₀cycloalkylcycloalkyl, C₅-C₁₀ alkylcycloalkylalkyl or C₃-C₆ cycloalkenyl,each unsubstituted or substituted with at least one substituentindependently selected from the group consisting of halogen, cyano,nitro, CHO, C(═O)OH, C(═O)NH₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl, C₁-C₄alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₂-C₄alkoxyalkyl, C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆alkylcarbonyloxy, C₂-C₆ alkylcarbonylthio, C₂-C₆ alkylaminocarbonyl,C₃-C₈ dialkylaminocarbonyl and C₃-C₆ trialkylsilyl; or phenyl or a 5- or6-membered heteroaromatic ring, each unsubstituted or substituted withat least one substituent independently selected from the groupconsisting of C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₂-C₆alkynyl, C₃-C₈ cycloalkyl, C₄-C₈ alkylcycloalkyl, C₄-C₈ cycloalkylalkyl,C₆-C₁₀ cycloalkylcycloalkyl, C₅-C₁₀ alkylcycloalkylalkyl, C₃-C₆cycloalkenyl, halogen, cyano, nitro, CHO, C(═O)OH, C(═O)NH₂, C₁-C₄alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄haloalkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆cycloalkylamino, C₂-C₄ alkoxyalkyl, C₂-C₄ alkylcarbonyl, C₂-C₆alkoxycarbonyl, C₂-C₆ alkylcarbonyloxy, C₂-C₆ alkylcarbonylthio, C₂-C₆alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl and C₃-C₆ trialkylsilyl;each R¹² and R¹³ is independently C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆alkynyl, C₃-C₈ cycloalkyl, C₄-C₈ alkylcycloalkyl, C₄-C₈ cycloalkylalkyl,C₆-C₁₀ cycloalkylcycloalkyl, C₅-C₁₀ alkylcycloalkylalkyl or C₃-C₆cycloalkenyl, each unsubstituted or substituted with at least onesubstituent independently selected from the group consisting of halogen,cyano, nitro, CHO, C(═O)OH, C(═O)NH₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy,C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl, C₁-C₄alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₂-C₄alkoxyalkyl, C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆alkylcarbonyloxy, C₂-C₆ alkylcarbonylthio, C₂-C₆ alkylaminocarbonyl,C₃-C₈ dialkylaminocarbonyl and C₃-C₆ trialkylsilyl; or phenyl or a 5- or6-membered heteroaromatic ring, each unsubstituted or substituted withat least one substituent independently selected from the groupconsisting of C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₂-C₆alkynyl, C₃-C₈ cycloalkyl, C₄-C₈ alkylcycloalkyl, C₄-C₈ cycloalkylalkyl,C₆-C₁₀ cycloalkylcycloalkyl, C₅-C₁₀ alkylcycloalkylalkyl, C₃-C₆cycloalkenyl, halogen, cyano, nitro, CHO, C(═O)OH, C(═O)NH₂, C₁-C₄alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄haloalkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆cycloalkylamino, C₂-C₄ alkoxyalkyl, C₂-C₄ alkylcarbonyl, C₂-C₆alkoxycarbonyl, C₂-C₆ alkylcarbonyloxy, C₂-C₆ alkylcarbonylthio, C₂-C₆alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl and C₃-C₆ trialkylsilyl;or R¹² and R¹³ are taken together with the nitrogen atom to which theyare attached to form a 3- to 7-membered ring containing ring membersselected from carbon atoms and up to 2 heteroatoms independentlyselected from one O, one S, and up to 2 N, wherein up to 2 carbon atomring members are independently selected from C(═O) and C(═S) and thesulfur atom ring member is selected from S, S(O) or S(O)₂, said ringoptionally substituted with up to 4 substituents independently selectedfrom the group consisting of halogen, cyano and C₁-C₄ alkyl; each R¹⁴ isindependently halogen, cyano, hydroxy, amino, nitro, SF₅, OCN, SCN, CHO,C(═O)OH, C(═O)NH₂, C(═S)NH₂, SO₂NH₂, C(═O)R¹⁸, C(═O)OR¹⁸, NHR¹⁸,NR¹⁸R¹⁹, C(═O)NR²¹R¹⁹, C(═O)NR²¹NR²²R²³, C(═S)NR²¹R¹⁹, SO₂NR²¹R¹⁹,OC(═O)R²¹, OC(═O)OR¹⁸, OC(═O)NR²¹R¹⁹, N(R²¹)C(═O)R²¹, N(R²¹)C(═O)OR¹⁹,N(R²¹)C(═O)NR²¹R²², OSO₂R¹⁸, OSO₂NR²¹R²², NR²¹SO₂R¹⁸, NR²¹SO₂NR²¹R²²,Si(R¹⁸R¹⁹R²⁰), C(═NR²¹)R²², C(═NOR²¹)R²², C(═NNR²¹R²²)R²³,C(═NN(C(═O)R¹⁹)R²¹)R²², C(═NN(C(═O)OR¹⁹)R²¹)R²², ON═CR²¹R²², ONR²¹R²²,S(═O)(═NR²¹)R²², SO₂NR²¹C(═O)NR²²R²³, P(═X²)R¹⁸R¹⁹, OP(═X²)R¹⁸R¹⁹,OP(═X²)(OR¹⁸)R¹⁹, OP(═X²)(OR¹⁸)OR¹⁹, N═CR²¹R²², NR²¹N═CR²²R²³,NR²¹NR²²R²³, NR²¹C(═X²)NR²²R²³, NR²¹C(═NR²¹)NR²²R²³,NR²¹NR²¹C(═X²)NR²²R²³, NR²¹NR²¹SO₂NR²²R²³, Z¹Q^(t) or Z¹Q^(i)Z¹Q^(t); orC₁-C₈ alkyl, C₂-C₈ alkenyl, C₂-C₈ alkenyl, C₃-C₁₀ cycloalkyl, C₄-C₁₀alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₆-C₁₄ cycloalkylcycloalkyl,C₅-C₁₀ alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl, C₁-C₈ alkoxy, C₃-C₈cycloalkoxy, C₄-C₁₀ cycloalkylalkoxy, C₂-C₈ alkenyloxy, C₂-C₈alkynyloxy, C₁-C₈ alkylthio, C₁-C₈ alkylsulfinyl, C₁-C₈ alkylsulfonyl,C₃-C₈ cycloalkylthio, C₃-C₈ cycloalkylsulfinyl, C₃-C₈cycloalkylsulfonyl, C₄-C₁₀ cycloalkylalkylthio, C₄-C₁₀cycloalkylalkylsulfinyl, C₄-C₁₀ cycloalkylalkylsulfonyl, C₂-C₈alkenylthio, C₂-C₈ alkenylsulfinyl, C₂-C₈ alkenylsulfonyl, C₂-C₈alkynylthio, C₂-C₈ alkynylsulfinyl or C₂-C₈ alkynylsulfonyl, eachunsubstituted or substituted with at least one substituent independentlyselected from R¹⁷; or two R¹⁴ substituents on adjacent ring atoms aretaken together with the adjacent ring atoms to form a 5- to 7-memberedcarbocyclic or heterocyclic ring, each ring containing ring membersselected from carbon atoms and up to 3 heteroatoms independentlyselected from up to 2 O, up to 2 S, and up to 3 N, wherein up to 2carbon atom ring members are independently selected from C(═O) and C(═S)and the sulfur atom ring members are independently selected fromS(═O)_(n), each ring optionally substituted with up to 3 substituentsindependently selected from the group consisting of halogen, cyano,hydroxy, amino, nitro, C(═O)OH, C(═O)NH₂, SO₂NH₂, C₁-C₄ alkyl, C₁-C₄haloalkyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₂-C₄haloalkynyl, C₃-C₇ cycloalkyl, C₃-C₇ halocycloalkyl, C₄-C₈alkylcycloalkyl, C₄-C₈ haloalkylcycloalkyl, C₄-C₈ cycloalkylalkyl, C₄-C₈halocycloalkylalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₂-C₆alkoxycarbonyl, C₂-C₆ haloalkoxycarbonyl, C₂-C₆ alkylcarbonyl and C₂-C₆haloalkylcarbonyl; each X² is independently O or S; each Z¹ isindependently a direct bond, O, S(O)_(n), NR⁶, C(R⁷)₂, C(R⁷)═C(R⁷),C(R⁷)₂O, OC(R⁷)₂, C(═X¹), C(═X¹)E, EC(═X¹), C(═NOR⁸) or C(═NN(R⁶)₂);each Q^(i) is independently a 3- to 10-membered ring or a 7- to11-membered ring system, each ring or ring system containing ringmembers selected from carbon atoms and up to 4 heteroatoms independentlyselected from up to 2 O, up to 2 S, and up to 4 N, wherein up to 3carbon atom ring members are independently selected from C(═O) and C(═S)and the sulfur atom ring members are independently selected fromS(═O)_(u)(═NR²⁴)_(z), each ring or ring system optionally substitutedwith up to 4 substituents independently selected from the groupconsisting of halogen, cyano, nitro, CHO, C(═O)OH, C(═O)NH₂, C(═O)R¹⁰,C(═O)OR¹¹, C(═O)NR¹²R¹³, OR¹¹, S(O)_(n)R¹⁰, SO₂NR¹²R¹³, Si(R¹⁰)₃ andR¹⁶; each Q^(t) is independently a 3- to 10-membered ring or a 7- to11-membered ring system, each ring or ring system containing ringmembers selected from carbon atoms and up to 4 heteroatoms independentlyselected from up to 2 O, up to 2 S, and up to 4 N, wherein up to 3carbon atom ring members are independently selected from C(═O) and C(═S)and the sulfur atom ring members are independently selected fromS(═O)_(u)(═NR²⁴)_(z), each ring or ring system optionally substitutedwith up to 5 substituents independently selected from the groupconsisting of halogen, cyano, nitro, CHO, C(═O)OH, C(═O)NH₂, C(═O)R¹⁰,C(═O)OR¹¹, C(═O)NR¹²R¹³, C(═O)NR²¹NR²²R²³, OR¹¹, S(O)_(n)R¹⁰ SO₂NR¹²R¹³,S(═O)(═NR²¹)R²², Si(R¹⁰)₃ and R¹⁶; each R¹⁵ is independently halogen,cyano, hydroxy, amino, nitro, SF₅, OCN, SCN, CHO, C(═O)OH, C(═O)NH₂,C(═S)NH₂, SO₂NH₂, C(═O)R¹⁸, C(═O)OR¹⁸, NHR¹⁸, NR¹⁸R¹⁹, C(═O)NR²¹R¹⁹,C(═O)NR²¹NR²²R²³, C(═S)NR²¹R¹⁹, SO₂NR²¹R¹⁹, S(═O)(═NR²¹)R²², OC(═O)R²¹,OC(═O)OR¹⁸, OC(═O)NR²¹R¹⁹, N(R²¹)C(═O)R²¹, N(R²¹)C(═O)OR¹⁹,N(R²¹)C(═O)NR²¹R²², OSO₂R¹⁸, OSO₂NR²¹R²², NR²¹SO₂R¹⁸, NR²¹SO₂NR²¹R²²,Si(R¹⁸R¹⁹R²⁰) or Z¹ Q^(t); or C₁-C₈ alkyl, C₂-C₈ alkenyl, C₂-C₈ alkynyl,C₃-C₁₀ cycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl,C₆-C₁₄ cycloalkylcycloalkyl, C₅-C₁₀ alkylcycloalkylalkyl, C₃-C₈cycloalkenyl, C₁-C₈ alkoxy, C₃-C₈ cycloalkoxy, C₄-C₁ cycloalkylalkoxy,C₂-C₈ alkenyloxy, C₂-C₈ alkynyloxy, C₁-C₈ alkylthio, C₁-C₈alkylsulfinyl, C₁-C₈ alkylsulfonyl, C₃-C₈ cycloalkylthio, C₃-C₈cycloalkylsulfinyl, C₃-C₈ cycloalkylsulfonyl, C₄-C₁₀cycloalkylalkylthio, C₄-C₁₀ cycloalkylalkylsulfinyl, C₄-C₁cycloalkylalkylsulfonyl, C₂-C₈ alkenylthio, C₂-C₈ alkenylsulfinyl, C₂-C₈alkenylsulfonyl, C₂-C₈ alkynylthio, C₂-C₈ alkynylsulfinyl or C₂-C₈alkynylsulfonyl, each unsubstituted or substituted with at least onesubstituent independently selected from R¹⁷; or two R¹⁵ substituents onadjacent ring atoms are taken together with the adjacent ring atoms toform a 5- to 7-membered carbocyclic or heterocyclic ring, each ringcontaining ring members selected from carbon atoms and up to 3heteroatoms independently selected from up to 2 O, up to 2 S, and up to3 N, wherein up to 2 carbon atom ring members are independently selectedfrom C(═O) and C(═S) and the sulfur atom ring members are independentlyselected from S(═O)_(n), each ring optionally substituted with up to 3substituents independently selected from the group consisting ofhalogen, cyano, hydroxy, amino, nitro, C(═O)OH, C(═O)NH₂, SO₂NH₂, C₁-C₄alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl,C₂-C₄ haloalkynyl, C₃-C₇ cycloalkyl, C₃-C₇ halocycloalkyl, C₄-C₈alkylcycloalkyl, C₄-C₈ haloalkylcycloalkyl, C₄-C₈ cycloalkylalkyl, C₄-C₈halocycloalkylalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₂-C₆alkoxycarbonyl, C₂-C₆ haloalkoxycarbonyl, C₂-C₆ alkylcarbonyl and C₂-C₆haloalkylcarbonyl; each R¹⁶ is independently C₁-C₆ alkyl, C₂-C₆ alkenyl,C₂-C₆ alkynyl, C₃-C₈ cycloalkyl, C₄-C₈ alkylcycloalkyl, C₄-C₈cycloalkylalkyl, C₆-C₁₀ cycloalkylcycloalkyl, C₅-C₁₀alkylcycloalkylalkyl or C₃-C₆ cycloalkenyl, each unsubstituted orsubstituted with at least one substituent independently selected fromthe group consisting of halogen, cyano, nitro, CHO, C(═O)OH, C(═O)NH₂,C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl,C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄haloalkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆cycloalkylamino, C₂-C₄ alkoxyalkyl, C₂-C₄ alkylcarbonyl, C₂-C₆alkoxycarbonyl, C₂-C₆ alkylcarbonyloxy, C₂-C₆ alkylcarbonylthio, C₂-C₆alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl and C₃-C₆ trialkylsilyl;or phenyl or a 5- or 6-membered heteroaromatic ring, each unsubstitutedor substituted with at least one substituent independently selected fromthe group consisting of C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₈cycloalkyl, C₄-C₈ alkylcycloalkyl, C₄-C₈ cycloalkylalkyl, C₆-C₁₀cycloalkylcycloalkyl, C₅-C₁₀ alkylcycloalkylalkyl, C₃-C₆ cycloalkenyl,halogen, cyano, nitro, CHO, C(═O)OH, C(═O)NH₂, C₁-C₄ alkoxy, C₁-C₄haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl,C₁-C₄ haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl,C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₂-C₄alkoxyalkyl, C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆alkylcarbonyloxy, C₂-C₆ alkylcarbonylthio, C₂-C₆ alkylaminocarbonyl,C₃-C₈ dialkylaminocarbonyl and C₃-C₆ trialkylsilyl; each R¹⁷ isindependently halogen, cyano, nitro, OH, CHO, C(═O)OH, C(═O)NH₂,C(═O)R¹⁰, C(═O)OR¹¹, C(═O)NR¹²R¹³, OR¹¹, S(O)_(n)R¹⁰, SO₂NR¹²R¹³,Si(R¹⁰)₃ or Z¹ Q^(t); each R¹⁸, R¹⁹ and R²⁰ is independently Q^(t); orC₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₈ cycloalkyl, C₄-C₈alkylcycloalkyl, C₄-C₈ cycloalkylalkyl, C₆-C₁₀ cycloalkylcycloalkyl,C₅-C₁₀ alkylcycloalkylalkyl or C₃-C₆ cycloalkenyl, each unsubstituted orsubstituted with at least one substituent independently selected fromR¹⁷; each R²¹ is independently Q^(t) or H; or C₁-C₆ alkyl, C₂-C₆alkenyl, C₂-C₆ alkynyl, C₃-C₈ cycloalkyl, C₄-C₈ alkylcycloalkyl, C₄-C₈cycloalkylalkyl, C₆-C₁₀ cycloalkylcycloalkyl, C₅-C₁₀alkylcycloalkylalkyl or C₃-C₆ cycloalkenyl, each unsubstituted orsubstituted with at least one substituent independently selected fromR¹⁷; each R²² and R²³ is independently Q^(t) or H; or C₁-C₆ alkyl, C₂-C₆alkenyl, C₂-C₆ alkynyl, C₃-C₈ cycloalkyl, C₄-C₈ alkylcycloalkyl, C₄-C₈cycloalkylalkyl, C₆-C₁₀ cycloalkylcycloalkyl, C₅-C₁₀alkylcycloalkylalkyl or C₃-C₆ cycloalkenyl, each unsubstituted orsubstituted with at least one substituent independently selected fromR¹⁷; or R²² and R²³ are taken together with the nitrogen atom to whichthey are attached to form a 3- to 7-membered ring containing ringmembers selected from carbon atoms and up to 2 heteroatoms independentlyselected from one O, one S, and up to 2 N, wherein up to 2 carbon atomring members are independently selected from C(═O) and C(═S) and thesulfur atom ring member is selected from S, S(O) or S(O)₂, said ringoptionally substituted with up to 4 substituents independently selectedfrom the group consisting of halogen, cyano and C₁-C₄ alkyl; each R²⁴ isindependently H, cyano, OCN, SCN, CHO, C(═O)OH, C(═O)NH₂, C(═S)NH₂,SO₂NH₂, C(═O)R¹⁸, C(═O)OR¹⁸, NHR¹⁸, NR¹⁸R¹⁹, C(═O)NR²¹R¹⁹, C(═S)NR²¹R¹⁹,SO₂NR²¹R¹⁹, OC(═O)R²¹, OC(═O)OR¹⁸, OC(═O)NR²¹R¹⁹, N(R²¹)C(═O)R²¹,N(R²¹)C(═O)OR¹⁹, N(R²¹)C(═O)NR²¹R²², OSO₂R¹⁸, OSO₂NR²¹R²², NR²¹SO₂R¹⁸,NR²¹SO₂NR²¹R²², Si(R¹⁸R¹⁹R²⁰) or Z¹ Q^(t); or C₁-C₈ alkyl, C₂-C₈alkenyl, C₂-C₈ alkynyl, C₃-C₁₀ cycloalkyl, C₄-C₁₀ alkylcycloalkyl,C₄-C₁₀ cycloalkylalkyl, C₆-C₁₄ cycloalkylcycloalkyl, C₅-C₁₀alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl, C₁-C₈ alkoxy, C₃-C₈cycloalkoxy, C₄-C₁₀ cycloalkylalkoxy, C₂-C₈ alkenyloxy, C₂-C₈alkynyloxy, C₁-C₈ alkylthio, C₁-C₈ alkylsulfinyl, C₁-C₈ alkylsulfonyl,C₃-C₈ cycloalkylthio, C₃-C₈ cycloalkylsulfinyl, C₃-C₈cycloalkylsulfonyl, C₄-C₁₀ cycloalkylalkylthio, C₄-C₁₀cycloalkylalkylsulfinyl, C₄-C₁₀ cycloalkylalkylsulfonyl, C₂-C₈alkenylthio, C₂-C₈ alkenylsulfinyl, C₂-C₈ alkenylsulfonyl, C₂-C₈alkynylthio, C₂-C₈ alkynylsulfinyl or C₂-C₈ alkynylsulfonyl, eachunsubstituted or substituted with at least one substituent independentlyselected from R¹⁷; a is 1, 2 or 3; each n is independently 0, 1 or 2;and u and z in each instance of S(═O)_(u)(═NR²⁴)_(z) are independently0, 1 or 2, provided that the sum of u and z in each instance ofS(═O)_(u)(═NR²⁴)_(z) is 0, 1 or 2; provided that when R^(3c) is H or F,and R^(3d) is H, F, CF₂H or CF₃, then at least one of R^(3a) or R^(3b)is other than H; and at least one additional component selected from thegroup consisting of surfactants, solid diluents and liquid diluents. 2.The composition of claim 1 further comprising at least one additionalbiologically active compound or agent.
 3. The composition of claim 2wherein the at least one additional biologically active compound oragent is selected from the group consisting of abamectin, acephate,acequinocyl, acetamiprid, acrinathrin, amidoflumet, amitraz, avermectin,azadirachtin, azinphos-methyl, bensultap, bifenthrin, bifenazate,bistrifluron, borate, buprofezin, cadusafos, carbaryl, carbofuran,cartap, carzol, chlorantraniliprole, chlorfenapyr, chlorfluazuron,chlorpyrifos, chlorpyrifos-methyl, chromafenozide, clofentezin,clothianidin, cyantraniliprole, cyflumetofen, cyfluthrin,beta-cyfluthrin, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin,cypermethrin, alpha-cypermethrin, zeta-cypermethrin, cyromazine,deltamethrin, diafenthiuron, diazinon, dieldrin, diflubenzuron,dimefluthrin, dimehypo, dimethoate, dinotefuran, diofenolan, emamectin,endosulfan, esfenvalerate, ethiprole, etofenprox, etoxazole, fenbutatinoxide, fenothiocarb, fenoxycarb, fenpropathrin, fenvalerate, fipronil,flonicamid, flubendiamide, flucythrinate, flufenerim, flufenoxuron,fluvalinate, tau-fluvalinate, fonophos, formetanate, fosthiazate,halofenozide, hexaflumuron, hexythiazox, hydramethylnon, imidacloprid,indoxacarb, insecticidal soaps, isofenphos, lufenuron, malathion,metaflumizone, metaldehyde, methamidophos, methidathion, methiodicarb,methomyl, methoprene, methoxychlor, metofluthrin, monocrotophos,methoxyfenozide, nitenpyram, nithiazine, novaluron, noviflumuron,oxamyl, parathion, parathion-methyl, permethrin, phorate, phosalone,phosmet, phosphamidon, pirimicarb, profenofos, profluthrin, propargite,protrifenbute, pymetrozine, pyrafluprole, pyrethrin, pyridaben,pyridalyl, pyrifluquinazon, pyriprole, pyriproxyfen, rotenone,ryanodine, spinetoram, spinosad, spirodiclofen, spiromesifen,spirotetramat, sulprofos, sulfoxaflor, tebufenozide, tebufenpyrad,teflubenzuron, tefluthrin, terbufos, tetrachlorvinphos, tetramethrin,thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, tolfenpyrad,tralomethrin, triazamate, trichlorfon, triflumuron, Bacillusthuringiensis delta-endotoxins, entomopathogenic bacteria,entomopathogenic viruses and entomopathogenic fungi.
 4. A compositioncomprising a compound of Formula 1 that is selected from the groupconsisting of:

and at least one additional component selected from the group consistingof surfactants, solid diluents and liquid diluents.
 5. The compositionof claim 4 further comprising at least one additional biologicallyactive compound or agent.
 6. The composition of claim 5 wherein the atleast one additional biologically active compound or agent is selectedfrom the group consisting of abamectin, acephate, acequinocyl,acetamiprid, acrinathrin, amidoflumet, amitraz, avermectin,azadirachtin, azinphos-methyl, bensultap, bifenthrin, bifenazate,bistrifluron, borate, buprofezin, cadusafos, carbaryl, carbofuran,cartap, carzol, chlorantraniliprole, chlorfenapyr, chlorfluazuron,chlorpyrifos, chlorpyrifos-methyl, chromafenozide, clofentezin,clothianidin, cyantraniliprole, cyflumetofen, cyfluthrin,beta-cyfluthrin, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin,cypermethrin, alpha-cypermethrin, zeta-cypermethrin, cyromazine,deltamethrin, diafenthiuron, diazinon, dieldrin, diflubenzuron,dimefluthrin, dimehypo, dimethoate, dinotefuran, diofenolan, emamectin,endosulfan, esfenvalerate, ethiprole, etofenprox, etoxazole, fenbutatinoxide, fenothiocarb, fenoxycarb, fenpropathrin, fenvalerate, fipronil,flonicamid, flubendiamide, flucythrinate, flufenerim, flufenoxuron,fluvalinate, tau-fluvalinate, fonophos, formetanate, fosthiazate,halofenozide, hexaflumuron, hexythiazox, hydramethylnon, imidacloprid,indoxacarb, insecticidal soaps, isofenphos, lufenuron, malathion,metaflumizone, metaldehyde, methamidophos, methidathion, methiodicarb,methomyl, methoprene, methoxychlor, metofluthrin, monocrotophos,methoxyfenozide, nitenpyram, nithiazine, novaluron, noviflumuron,oxamyl, parathion, parathion-methyl, permethrin, phorate, phosalone,phosmet, phosphamidon, pirimicarb, profenofos, profluthrin, propargite,protrifenbute, pymetrozine, pyrafluprole, pyrethrin, pyridaben,pyridalyl, pyrifluquinazon, pyriprole, pyriproxyfen, rotenone,ryanodine, spinetoram, spinosad, spirodiclofen, spiromesifen,spirotetramat, sulprofos, sulfoxaflor, tebufenozide, tebufenpyrad,teflubenzuron, tefluthrin, terbufos, tetrachlorvinphos, tetramethrin,thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, tolfenpyrad,tralomethrin, triazamate, trichlorfon, triflumuron, Bacillusthuringiensis delta-endotoxins, entomopathogenic bacteria,entomopathogenic viruses and entomopathogenic fungi.
 7. The compositionof claim 4 wherein the compound of Formula 1 is


8. The composition of claim 7 further comprising at least one additionalbiologically active compound or agent.
 9. The composition of claim 8wherein the at least one additional biologically active compound oragent is selected from the group consisting of abamectin, acephate,acequinocyl, acetamiprid, acrinathrin, amidoflumet, amitraz, avermectin,azadirachtin, azinphos-methyl, bensultap, bifenthrin, bifenazate,bistrifluron, borate, buprofezin, cadusafos, carbaryl, carbofuran,cartap, carzol, chlorantraniliprole, chlorfenapyr, chlorfluazuron,chlorpyrifos, chlorpyrifos-methyl, chromafenozide, clofentezin,clothianidin, cyantraniliprole, cyflumetofen, cyfluthrin,beta-cyfluthrin, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin,cypermethrin, alpha-cypermethrin, zeta-cypermethrin, cyromazine,deltamethrin, diafenthiuron, diazinon, dieldrin, diflubenzuron,dimefluthrin, dimehypo, dimethoate, dinotefuran, diofenolan, emamectin,endosulfan, esfenvalerate, ethiprole, etofenprox, etoxazole, fenbutatinoxide, fenothiocarb, fenoxycarb, fenpropathrin, fenvalerate, fipronil,flonicamid, flubendiamide, flucythrinate, flufenerim, flufenoxuron,fluvalinate, tau-fluvalinate, fonophos, formetanate, fosthiazate,halofenozide, hexaflumuron, hexythiazox, hydramethylnon, imidacloprid,indoxacarb, insecticidal soaps, isofenphos, lufenuron, malathion,metaflumizone, metaldehyde, methamidophos, methidathion, methiodicarb,methomyl, methoprene, methoxychlor, metofluthrin, monocrotophos,methoxyfenozide, nitenpyram, nithiazine, novaluron, noviflumuron,oxamyl, parathion, parathion-methyl, permethrin, phorate, phosalone,phosmet, phosphamidon, pirimicarb, profenofos, profluthrin, propargite,protrifenbute, pymetrozine, pyrafluprole, pyrethrin, pyridaben,pyridalyl, pyrifluquinazon, pyriprole, pyriproxyfen, rotenone,ryanodine, spinetoram, spinosad, spirodiclofen, spiromesifen,spirotetramat, sulprofos, sulfoxaflor, tebufenozide, tebufenpyrad,teflubenzuron, tefluthrin, terbufos, tetrachlorvinphos, tetramethrin,thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, tolfenpyrad,tralomethrin, triazamate, trichlorfon, triflumuron, Bacillusthuringiensis delta-endotoxins, entomopathogenic bacteria,entomopathogenic viruses and entomopathogenic fungi.
 10. The compositionof claim 1 wherein in the compound of Formula 1 X is O; Y is O; Z is adirect bond, C(═X¹) or C(═X¹)E; X¹ is O; E is O; R² is C(═O)OR¹⁸; orC₁-C₈ alkyl optionally substituted with halogen; or a 3- to 10-memberedring or a 7- to 11-membered ring system, each ring or ring systemcontaining ring members selected from carbon atoms and up to 4heteroatoms independently selected from up to 2 O, up to 2 S, and up to4 N, wherein up to 3 carbon atom ring members are independently selectedfrom C(═O) and C(═S) and the sulfur atom ring members are independentlyselected from S(═O)_(u)(═NR²⁴)_(z), each ring or ring system optionallysubstituted with up to 5 substituents independently selected from R¹⁵;R^(3a), R^(3b), R^(3c) are independently H or halogen; R^(3d) ishalogen, C₁-C₈ alkyl, C₁-C₈ alkoxy, C₁-C₈ haloalkyl or C₁-C₈ haloalkoxy;or R^(3c) and R^(3d) are taken together to form a 5- to 7-memberedcarbocyclic or heterocyclic ring, each ring containing ring membersselected from carbon atoms and up to 3 heteroatoms independentlyselected from up to 2 O, up to 2 S, and up to 3 N, wherein up to 2carbon atom ring members are independently selected from C(═O) and C(═S)and the sulfur atom ring members are independently selected fromS(═O)_(n), each ring optionally substituted with up to 3 substituentsindependently selected from the group consisting of halogen, cyano,hydroxy, amino, nitro, C(═O)OH, C(═O)NH₂, SO₂NH₂, C₁-C₄ alkyl, C₁-C₄haloalkyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₂-C₄haloalkynyl, C₃-C₇ cycloalkyl, C₃-C₇ halocycloalkyl, C₄-C₈alkylcycloalkyl, C₄-C₈ haloalkylcycloalkyl, C₄-C₈ cycloalkylalkyl, C₄-C₈halocycloalkylalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₂-C₆alkoxycarbonyl, C₂-C₆ haloalkoxycarbonyl, C₂-C₆ alkylcarbonyl and C₂-C₆haloalkylcarbonyl; R⁴ and R⁵ are H; and a is
 1. 11. The composition ofclaim 10 wherein in the compound of Formula 1 R¹ is phenyl or a 5- or6-membered heteroaromatic ring, each optionally substituted with up to 3substituents independently selected from R¹⁴; R¹⁴ is halogen, cyano,C(═O)OR¹⁸, C(═O) NR²¹R¹⁹, C(═NOR²¹)R²² or Z¹Q^(t); or C₁-C₈ alkyl, C₁-C₈alkoxy or C₁-C₈ alkylthio, each optionally substituted with halogen; R²¹is C₁-C₄ alkyl; R²² is C₁-C₄ alkyl; Z is a direct bond; each Z¹ isindependently a direct bond or O; and each Q^(t) is independently phenylor a 5- or 6-membered heteroaromatic ring, each optionally substitutedwith up to 5 substituents independently selected from the groupconsisting of halogen, cyano, nitro, CHO, C(═O)OH, C(═O)NH₂, C(═O)R¹⁰,C(═O)OR¹¹, C(═O)NR¹²R¹³, C(═O)NR²¹NR²²R²³, OR¹¹, S(O)_(n)R¹⁰,SO₂NR¹²R¹³, S(═O)(═NR²¹)R²², Si(R¹⁰)₃ and R¹⁶.
 12. The composition ofclaim 11 wherein in the compound of Formula 1 R² is pyridinyl,pyrimidinyl, oxazolyl or thiazolyl, each optionally substituted with upto 3 substituents independently selected from the group consisting ofhalogen and C₁-C₄ alkyl.
 13. The composition of claim 12 wherein in thecompound of Formula 1 R¹ is phenyl or pyridinyl, each optionallysubstituted with up to 3 substituents independently selected from R¹⁴;and each Q^(t) is independently phenyl, pyridinyl or pyrimidinyl, eachoptionally substituted with up to 5 substituents independently selectedfrom the group consisting of halogen, cyano, C₁-C₄ alkyl, C₁-C₄haloalkyl, C₁-C₄ alkoxy and C₁-C₄ haloalkoxy.
 14. The composition ofclaim 13 wherein in the compound of Formula 1 R^(3a), R^(3b) and R^(3c)are H; and R^(3d) is halogen, C₁-C₄ alkyl or C₁-C₄ alkoxy.